fix(fix): revert the 10-second ticker to 10m after forgetting to revert it after testing

* feat(tui): remake parts of the tui

* chore(tui): remove unused newViewport helper

.github/workflows/ci.yml

@@ -0,0 +1,65 @@
+name: CI
+
+on:
+  pull_request:
+    branches: [master]
+
+jobs:
+  check:
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v6
+
+      - uses: actions/setup-go@v6
+        with:
+          go-version-file: go.mod
+
+      - name: Build
+        run: go build ./...
+
+      - name: Vet
+        run: go vet ./...
+
+      - name: Format check
+        run: |
+          unformatted=$(gofmt -l $(go list -f '{{.Dir}}' ./...))
+          if [ -n "$unformatted" ]; then
+            echo "These files need gofmt:"
+            echo "$unformatted"
+            exit 1
+          fi
+
+      - name: Lint
+        if: ${{ !env.ACT }}
+        uses: golangci/golangci-lint-action@v7
+        with:
+          version: v2.4.0
+
+      - name: Install tparse
+        run: go install github.com/mfridman/tparse@v0.18.0
+
+      - name: Test (race detector)
+        run: |
+          set +e
+          go tool gotestsum \
+            --format pkgname \
+            --format-icons hivis \
+            --hide-summary=skipped,output,errors,failed \
+            --jsonfile test-output.json \
+            --junitfile test-report.xml \
+            --packages="./..." \
+            -- -count=1 -race -covermode=atomic -coverprofile=coverage.out
+          rc=$?
+          echo
+          tparse -all -notests -slow 10 -file=test-output.json || true
+          exit $rc
+
+      - name: Upload test report 
+        if: always()
+        uses: actions/upload-artifact@v4
+        with:
+          name: test-report
+          path: |
+            test-output.json
+            test-report.xml
+            coverage.out

.github/workflows/deploy.yml

@@ -8,18 +8,10 @@ jobs:
   deploy:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v4
-      - uses: actions/setup-go@v5
+      - uses: actions/checkout@v6
+      - uses: actions/setup-go@v6
         with:
-          go-version: '1.23'
-      - name: Cache Go modules
-        uses: actions/cache@v4
-        with:
-          path: |
-            ~/go/pkg/mod
-            ~/.cache/go-build
-          key: ${{ runner.os }}-go-${{ hashFiles('go.sum') }}
-          restore-keys: ${{ runner.os }}-go-
+          go-version-file: go.mod
       - name: Run tests
         run: go test ./...
       - name: Deploy to server
@@ -30,6 +22,15 @@ jobs:
           key: ${{ secrets.SERVER_SSH_KEY }}
           port: ${{ secrets.SERVER_PORT }}
           script: |
+            set -euo pipefail
             cd ~/terminalShop
-            git pull
+            git fetch origin master
+            git reset --hard origin/master
+            deployed=$(git rev-parse HEAD)
+            expected="${{ github.sha }}"
+            if [ "$deployed" != "$expected" ]; then
+              echo "::error::deploy HEAD mismatch: box=$deployed expected=$expected"
+              exit 1
+            fi
             docker compose -f docker-compose.prod.yml up -d --build
+            echo "deploy verified: HEAD=$deployed"

.gitignore

@@ -5,6 +5,15 @@
 .env.example
 .env.prod
 
+docs/sca-psd2-compliance.md
+accept-a-payment/
+codemap/
+
+
+FULFILLMENT.md
+.tmp-gocache/
+.junie/
+
 # Build artifacts
 *.exe
 *.exe~
@@ -25,6 +34,8 @@ api/api-server
 *.out
 coverage.txt
 coverage.html
+test-output.json
+test-report.xml
 
 # Dependency directories
 vendor/
@@ -38,6 +49,8 @@ vendor/
 .DS_Store
 .claude/
 
+.understand-anything/
+
 # ssh config
 .ssh/
 
@@ -64,7 +77,6 @@ temp/
 
 # OS-specific
 Thumbs.db
-.DS_Store
 
 CONTRIBUTING.md
 
@@ -78,6 +90,7 @@ REFACTORING.md
 TODO.md
 NEXT.md
 test_stripe.go
+REFACTOR_PLAN.md
 
 
 codebase_graph.html
@@ -91,6 +104,19 @@ docs/
 # Migration state (if using a migration tool that creates state files)
 migrations/*.state
 
+gh-dash/
 
 
 
+loadtest/run.pid
+loadtest/run.err
+
+/00
+
+ROADMAP.md
+
+*.bak
+terminalshop.prod.*
+
+# Backup verification config (real values; example file is committed)
+scripts/backups/config.env

.golangci.yml

@@ -0,0 +1,16 @@
+version: "2"
+
+run:
+  timeout: 5m
+
+linters:
+  default: none
+  enable:
+    - errcheck
+    - govet
+    - ineffassign
+    - staticcheck
+    - unused
+  exclusions:
+    paths:
+      - terminal-shop-source

Makefile

@@ -0,0 +1,55 @@
+.PHONY: test test-pretty test-watch test-ci test-summary cover
+
+PKGS ?= ./...
+JSON_OUT ?= test-output.json
+JUNIT ?= test-report.xml
+COVER ?= coverage.out
+
+# Plain go test. Fastest, no extra deps loaded
+test:
+	go test $(PKGS)
+
+# Live pretty output. Groups by test name, reruns flakes once.
+# Hides gotestsum's plain-text summary; tparse renders failures instead.
+test-pretty:
+	@set +e; \
+	go tool gotestsum \
+		--format testname \
+		--format-icons hivis \
+		--hide-summary=skipped,output,errors,failed \
+		--rerun-fails=1 \
+		--jsonfile $(JSON_OUT) \
+		--packages="$(PKGS)" \
+		-- -count=1; \
+	rc=$$?; \
+	echo; \
+	tparse -all -notests -file=$(JSON_OUT) || true; \
+	exit $$rc
+
+# TDD loop: re-runs affected packages on file save.
+test-watch:
+	go tool gotestsum --watch --format testname --packages="$(PKGS)"
+
+# CI / pre-push: race + coverage + JSON + JUnit + tparse summary table
+test-ci:
+	@set +e; \
+	go tool gotestsum \
+		--format pkgname \
+		--format-icons hivis \
+		--hide-summary=skipped,output,errors,failed \
+		--jsonfile $(JSON_OUT) \
+		--junitfile $(JUNIT) \
+		--packages="$(PKGS)" \
+		-- -count=1 -race -covermode=atomic -coverprofile=$(COVER); \
+	rc=$$?; \
+	echo; \
+	tparse -all -notests -slow 10 -file=$(JSON_OUT) || true; \
+	exit $$rc
+
+# Replay last summary without re-running tests
+test-summary:
+	tparse -all -notests -file=$(JSON_OUT)
+
+# Open HTML coverage report from last `test-ci` run
+cover:
+	go tool cover -html=$(COVER)

README.md

@@ -4,10 +4,71 @@
 ssh sshops.uk
 ```
 
+## demo
+https://github.com/user-attachments/assets/daf895ac-2c01-4323-bf27-8d7829b9ddd5
+
 it's a coffee shop but in your terminal. you ssh in, browse the menu, chuck stuff in your cart, put in your address and card, and buy coffee without ever touching a browser. your ssh key is your account so there's no login or signup or any of that.
 
 made it because i thought it would be fun to see if you could build a real e-commerce flow that lives entirely in a terminal. turns out you can. heavily inspired by [terminal.shop](https://terminal.shop).
 
-running on Hetzner, behind Cloudflare.
+## what it actually does
 
-**tech:** Go, Bubbletea, Wish, Chi, PostgreSQL, Stripe, Shippo, Bring
+ssh in and you get a TUI. browse coffee, add to cart, save addresses, save cards. checkout charges your card via stripe and creates a real order. addresses get validated against shippo (US) or bring (Norway) before they're allowed in. cards are tokenized server side so the secret key never touches your terminal session. adding cards through the tui is coming soon, i just need to register a business and i have no money. webhooks from stripe reconcile order state if anything goes weird mid charge, and a cron job catches orders that got charged but never recorded because the server crashed.
+
+it's a real shop. you can actually buy coffee.
+
+## the stack
+
+**TUI + SSH.** Go with [Bubbletea](https://github.com/charmbracelet/bubbletea) for the terminal UI, [Wish](https://github.com/charmbracelet/wish) for the ssh server. every ssh session spawns its own bubbletea program. lipgloss for styling.
+
+**API.** Go again, [Chi](https://github.com/go-chi/chi) for routing. JWT auth where the token is exchanged for an ssh fingerprint, so the TUI authenticates by proving it has the same key the user ssh'd in with. no passwords anywhere.
+
+**Database.** SQLite via GORM. yeah just a file. it's fine. i back it up nightly with restic and the SQLite backup API so it's WAL safe even if a write is in flight. when traffic actually demands postgres i'll switch. the DSN prefix logic in `pkg/database/db.go` already handles both drivers.
+
+**Payments.** [Stripe](https://stripe.com). cards are tokenized server side, never raw card data on disk. webhooks handle async confirmations like 3DS, deferred charges, refunds. idempotency keys tied to order IDs so retries can't double charge.
+
+**Address validation.** [Shippo](https://goshippo.com) for US addresses, [Bring](https://www.bring.com) for Norway. invalid addresses get rejected before they hit the cart.
+
+## where it runs
+
+production lives on a single Hetzner VPS in Helsinki, behind [Caddy](https://caddyserver.com) which handles auto TLS so there's no nginx config to babysit. everything in docker compose. the API, caddy, and the whole observability stack run as separate compose stacks on the same box. public DNS only resolves the API and the marketing site, everything else is tailnet only.
+
+backups go to a second machine sitting in my house. that machine runs **Linux From Scratch** with a hand compiled kernel and a hand rolled ports repo i maintain myself with [scratchpkg](https://github.com/emmett1/scratchpkg). no docker, no apt, every binary built from a recipe i wrote. it also runs my self hosted [Gitea](https://gitea.com). it's got like 4 GB of RAM so it has to run lean. picked it because i wanted to learn how a linux box actually fits together when nobody's holding your hand.
+
+backup pipeline runs nightly. cron on the Hetzner box snapshots the SQLite db via the backup API, ships it over Tailscale SFTP to the LFS box with [restic](https://restic.net), encrypted and deduped. dual dead man switches, [healthchecks.io](https://healthchecks.io) and a Uptime Kuma push monitor, both go off if the cron silently dies.
+
+## observability
+
+probably the over engineered part. honestly built it because i wanted to learn the stack.
+
+**Prometheus** scrapes the API for the usual RED metrics plus custom counters like cart conversions, auth attempts, stripe events, log levels, orders created.
+
+**Grafana** sits in front of everything. tailnet only, no public DNS.
+
+**Loki + Promtail** for logs. promtail auto discovers every container via docker labels so anything new on the box is logged for free.
+
+**Tempo** for traces. the API exports OTLP via [otelchi](https://github.com/riandyrn/otelchi) on the inbound side and [otelhttp](https://pkg.go.dev/go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp) on outbound calls to stripe, shippo, bring. the GORM tracing plugin emits a span per SQL query.
+
+**Uptime Kuma** for blackbox checks. API health, TLS, backup target reachable.
+
+**Alerts** route through Grafana to a ntfy webhook to my phone.
+
+end to end, a request to `/api/v1/cart` shows up as one trace with the chi handler as the root, gorm queries as children, and outbound HTTP to stripe as a sibling. all one tempo span tree.
+
+## local dev
+
+```bash
+git clone https://github.com/marcusDenslow/terminalShop
+cd terminalShop
+cp .env.example .env  # fill in stripe test keys
+go run main.go        # ssh server on :23457
+go run api/main.go    # API on :8080
+ssh localhost -p 23457
+```
+
+uses SQLite by default so there's nothing to spin up.
+
+## inspiration
+
+[terminal.shop](https://terminal.shop) for the original idea and most of the patterns in `pkg/tui/`. their source is open and worth reading.
+# something

REFACTOR_PLAN.md

@@ -1,150 +0,0 @@
-# Refactor: Extract Flat Model State into Nested Page Structs
-
-## Context
-
-The TUI's `Model` struct has 40+ flat fields for page-specific state (cursors, viewports, form pointers, booleans). The reference implementation (`terminal-shop-source`) uses nested per-page state structs, which keeps related state grouped, simplifies page transitions, and makes it easier to add new pages. The `shopState` struct already follows this pattern — this refactor extends it to all other pages.
-
-This is a **pure refactoring** — no new features, no behavior changes. It unblocks future work (product variants, profile editing) by making the Model manageable.
-
----
-
-## New Struct Definitions (all in `model.go`)
-
-### `splashState` (3 fields, from Model)
-| Old Field | New Field |
-|-----------|-----------|
-| `splashDataReady` | `splash.dataReady` |
-| `splashDelayDone` | `splash.delayDone` |
-| `splashCursor` | `splash.cursor` |
-
-### `cartState` (3 fields, new struct)
-| Old Field | New Field |
-|-----------|-----------|
-| `CartCursor` | `cart.cursor` |
-| `cartVP` | `cart.viewport` |
-| `cartVPReady` | `cart.viewportReady` |
-
-### `shippingState` (5 fields, new struct)
-| Old Field | New Field |
-|-----------|-----------|
-| `ShippingForm` | `shipping.form` |
-| `ShippingView` | `shipping.view` |
-| `AddressCursor` | `shipping.addressCursor` |
-| `shippingVP` | `shipping.viewport` |
-| `shippingVPReady` | `shipping.viewportReady` |
-
-### `paymentState` (7 fields, new struct)
-| Old Field | New Field |
-|-----------|-----------|
-| `PaymentForm` | `payment.form` |
-| `PaymentView` | `payment.view` |
-| `CardCursor` | `payment.cardCursor` |
-| `CollectURL` | `payment.collectURL` |
-| `CollectCardCount` | `payment.collectCardCount` |
-| `paymentVP` | `payment.viewport` |
-| `paymentVPReady` | `payment.viewportReady` |
-
-### `accountState` (14 fields, new struct)
-| Old Field | New Field |
-|-----------|-----------|
-| `AccountCursor` | `account.cursor` |
-| `ScrollOffset` | `account.scrollOffset` |
-| `OrderViewState` | `account.orderViewState` |
-| `OrderCursor` | `account.orderCursor` |
-| `FaqFocused` | `account.faqFocused` |
-| `AddressListFocused` | `account.addressListFocused` |
-| `CardListFocused` | `account.cardListFocused` |
-| `AccountAddressCursor` | `account.addressCursor` |
-| `AccountCardCursor` | `account.cardCursor` |
-| `AccountAddressDeleting` | `account.addressDeleting` |
-| `AccountCardDeleting` | `account.cardDeleting` |
-| `SSHKeyListFocused` | `account.sshKeyListFocused` |
-| `AccountSSHKeyCursor` | `account.sshKeyCursor` |
-| `AccountSSHKeyDeleting` | `account.sshKeyDeleting` |
-
-### `reviewState` (2 fields, new struct)
-| Old Field | New Field |
-|-----------|-----------|
-| `CardJustAdded` | `review.cardJustAdded` |
-| `ReviewSuccess` | `review.success` |
-
-### `confirmState` (5 fields, new struct)
-| Old Field | New Field |
-|-----------|-----------|
-| `ConfirmTotal` | `confirm.total` |
-| `ConfirmItems` | `confirm.items` |
-| `ConfirmShipping` | `confirm.shipping` |
-| `confirmVP` | `confirm.viewport` |
-| `confirmVPReady` | `confirm.viewportReady` |
-
-### Fields that STAY on Model (shared across pages)
-`Cart`, `Coffees`, `SavedAddresses`, `SavedCards`, `SSHKeys`, `Orders`, `OrdersLoaded`, `SSHKeysLoaded`, `FAQs`, `ShippingInfo`, `SelectedCard`, `CheckingOut`, `lastCartUpdateID`, `User`, `AccessToken`, `APIClient`, `ErrorMsg`, `Loading`, all layout/resize/auth/rendering fields.
-
----
-
-## Execution Order (one struct at a time, compile+test after each)
-
-### Phase 1: `splashState` (simplest — 3 fields, 3 files)
-- Files: `model.go`, `update.go`, `splash.go`
-
-### Phase 2: `cartState` (3 fields, 3 files)
-- Files: `model.go`, `cart.go`, `confirmation.go` (resets cart cursor after checkout)
-
-### Phase 3: `confirmState` (5 fields, 1 file)
-- Files: `model.go`, `confirmation.go`
-
-### Phase 4: `reviewState` (2 fields, 2 files)
-- Files: `model.go`, `confirmation.go`, `payment_form.go`
-
-### Phase 5: `shippingState` (5 fields, 4 files)
-- Files: `model.go`, `shipping_form.go`, `update.go`, `footer.go`
-
-### Phase 6: `paymentState` (7 fields, 4 files)
-- Files: `model.go`, `payment_form.go`, `update.go`, `footer.go`
-
-### Phase 7: `accountState` (14 fields, 5 files — largest change)
-- Files: `model.go`, `account.go`, `views.go`, `footer.go`, `update.go`
-- Note: `ScrollOffset` moves here. All other pages use viewports, so the generic scroll block in `views.go` becomes account-only.
-
-### Phase 8: Add `*Switch()` methods + remove `resetPageState()`
-- Add `ShopSwitch()`, `CartSwitch()`, `AccountSwitch()`, `ShippingSwitch()`, `PaymentSwitch()`, `ReviewSwitch()` to `model.go`
-- Each calls `SwitchPage()`, zero-initializes its page state (`m.cart = cartState{}`), updates viewport
-- Replace `SwitchPage(X).resetPageState()` calls in `update.go`, `menu.go`, `confirmation.go`
-- Delete `resetPageState()`
-
----
-
-## Files Modified (summary)
-
-| File | Scope of Changes |
-|------|-----------------|
-| `pkg/tui/model.go` | Define structs, remove flat fields, add Switch methods, delete `resetPageState()` |
-| `pkg/tui/update.go` | Rename all field accesses, replace `SwitchPage().resetPageState()` with `*Switch()` |
-| `pkg/tui/cart.go` | `m.CartCursor` -> `m.cart.cursor`, viewport fields |
-| `pkg/tui/account.go` | 14 field renames to `m.account.*` |
-| `pkg/tui/shipping_form.go` | `m.ShippingForm` -> `m.shipping.form`, viewport/cursor fields |
-| `pkg/tui/payment_form.go` | `m.PaymentForm` -> `m.payment.form`, viewport/cursor fields |
-| `pkg/tui/confirmation.go` | confirm + review + cart cursor field renames |
-| `pkg/tui/views.go` | `m.ScrollOffset` -> `m.account.scrollOffset`, account field refs |
-| `pkg/tui/footer.go` | Multiple field renames for page-state reads |
-| `pkg/tui/menu.go` | Replace `SwitchPage().resetPageState()` with `*Switch()` |
-| `pkg/tui/splash.go` | `m.splashCursor` -> `m.splash.cursor` |
-| `pkg/tui/header.go` | No changes |
-| `pkg/tui/breadcrumbs.go` | No changes |
-| `pkg/tui/help.go` | No changes |
-| `pkg/tui/faq.go` | No changes |
-
----
-
-## Verification
-
-After each phase:
-1. `go build ./...` — must compile
-2. `go test ./pkg/tui/...` — existing tests pass
-3. After all phases complete, manual test:
-   - SSH in, verify splash -> shop transition
-   - Browse shop, add items to cart
-   - Full checkout: shipping -> payment -> review -> confirm
-   - Account page: orders, addresses, cards, SSH keys, FAQ tabs
-   - Menu (m) and help (?) modals
-   - Terminal resize during each page

api/doc.go

@@ -0,0 +1,3 @@
+// Command api is the HTTP backend: it boots the router, bolts on all the
+// middleware, and answers the requests the TUI throws at it.
+package main

api/handlers/addresses.go

@@ -2,7 +2,7 @@ package handlers
 
 import (
 	"encoding/json"
-	"log"
+	"log/slog"
 	"net/http"
 	"strconv"
 
@@ -16,6 +16,8 @@ import (
 	"terminalShop/pkg/utils"
 )
 
+func addressLog() *slog.Logger { return slog.With("component", "address") }
+
 type AddressHandler struct {
 	shippoKey   string
 	bringAPIUID string
@@ -33,20 +35,20 @@ func NewAddressHandler(shippoAPIKey, bringAPIUID, bringAPIKey string) *AddressHa
 
 // Retrieve all saved addresses for a user
 func (h *AddressHandler) GetAddresses(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var addresses []models.Address
 	db.Where("user_id = ?", userID).Order("is_default DESC, created_at DESC").Find(&addresses)
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"addresses": addresses,
 	})
 }
 
 func (h *AddressHandler) CreateAddress(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 
 	userID := middleware.UserIDFromContext(r.Context())
 
@@ -80,7 +82,7 @@ func (h *AddressHandler) CreateAddress(w http.ResponseWriter, r *http.Request) {
 			return
 		}
 		client := shippo.NewClient(h.shippoKey)
-		validated, err := client.ValidateAddress(shippo.Address{
+		validated, err := client.ValidateAddress(r.Context(), shippo.Address{
 			Name:    req.Name,
 			Street1: req.Street,
 			Street2: req.Street2,
@@ -91,7 +93,7 @@ func (h *AddressHandler) CreateAddress(w http.ResponseWriter, r *http.Request) {
 			Phone:   req.Phone,
 		})
 		if err != nil {
-			log.Printf("shippo address validation failed: %v", err)
+			addressLog().Warn("shippo address validation failed", "error", err, "country", "US")
 			utils.RespondError(w, http.StatusBadRequest, "INVALID_ADDRESS", "address is invalid", nil)
 			return
 		}
@@ -112,7 +114,7 @@ func (h *AddressHandler) CreateAddress(w http.ResponseWriter, r *http.Request) {
 			return
 		}
 		client := bring.NewClient(h.bringAPIUID, h.bringAPIKey)
-		validated, err := client.ValidateAddress(bring.Address{
+		validated, err := client.ValidateAddress(r.Context(), bring.Address{
 			Name:    req.Name,
 			Street1: req.Street,
 			Street2: req.Street2,
@@ -122,7 +124,7 @@ func (h *AddressHandler) CreateAddress(w http.ResponseWriter, r *http.Request) {
 			Phone:   req.Phone,
 		})
 		if err != nil {
-			log.Printf("bring address validation failed: %v", err)
+			addressLog().Warn("bring address validation failed", "error", err, "country", "NO")
 			utils.RespondError(w, http.StatusBadRequest, "INVALID_ADDRESS", "address is invalid", nil)
 			return
 		}
@@ -141,19 +143,25 @@ func (h *AddressHandler) CreateAddress(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
+	// remove existing addres with the same street addres
+	var existing models.Address
+	if err := db.Where("user_id = ? AND street = ?", userID, address.Street).First(&existing).Error; err == nil {
+		db.Delete(&existing)
+	}
+
 	if err := db.Create(&address).Error; err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to create address", nil)
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusCreated, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusCreated, map[string]any{
 		"address": address,
 	})
 }
 
 // DeleteAddress deltes a saved address
 func (h *AddressHandler) DeleteAddress(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	idStr := chi.URLParam(r, "id")
@@ -175,7 +183,7 @@ func (h *AddressHandler) DeleteAddress(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"message": "address successfully deleted",
 	})
 }
@@ -183,7 +191,7 @@ func (h *AddressHandler) DeleteAddress(w http.ResponseWriter, r *http.Request) {
 // Mark an address as the users default address
 
 func (h *AddressHandler) SetDefaultAddress(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	idStr := chi.URLParam(r, "id")
@@ -210,7 +218,7 @@ func (h *AddressHandler) SetDefaultAddress(w http.ResponseWriter, r *http.Reques
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"address": address,
 	})
 }

api/handlers/addresses_test.go

@@ -13,7 +13,7 @@ import (
 func setupAddressTestDB(t *testing.T) (string, models.User) {
 	t.Helper()
 	testDB := "test_addresses.db"
-	os.Remove(testDB)
+	_ = os.Remove(testDB)
 	database.ResetForTesting()
 
 	db, err := database.Connect(testDB)
@@ -42,7 +42,7 @@ func setupAddressTestDB(t *testing.T) (string, models.User) {
 
 func TestGetAddressesEmpty(t *testing.T) {
 	testDB, user := setupAddressTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	handler := NewAddressHandler("", "", "")
@@ -58,7 +58,7 @@ func TestGetAddressesEmpty(t *testing.T) {
 	var resp struct {
 		Success bool `json:"success"`
 		Data    struct {
-			Addresses []interface{} `json:"addresses"`
+			Addresses []any `json:"addresses"`
 		} `json:"data"`
 	}
 	if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
@@ -74,7 +74,7 @@ func TestGetAddressesEmpty(t *testing.T) {
 
 func TestGetAddressesIsolation(t *testing.T) {
 	testDB, user1 := setupAddressTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -105,7 +105,7 @@ func TestGetAddressesIsolation(t *testing.T) {
 			Addresses []models.Address `json:"addresses"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if len(resp.Data.Addresses) != 1 {
 		t.Fatalf("expexted 1 address for user1, got %d", len(resp.Data.Addresses))
@@ -117,7 +117,7 @@ func TestGetAddressesIsolation(t *testing.T) {
 
 func TestGetAddressesWithData(t *testing.T) {
 	testDB, user := setupAddressTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()

api/handlers/auth.go

@@ -2,8 +2,10 @@ package handlers
 
 import (
 	"encoding/json"
+	"log/slog"
 	"net/http"
 
+	"terminalShop/api/middleware"
 	"terminalShop/pkg/auth"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
@@ -12,6 +14,8 @@ import (
 	"gorm.io/gorm"
 )
 
+func authLog() *slog.Logger { return slog.With("component", "auth") }
+
 // AuthHandler handles authentication-related requests
 type AuthHandler struct {
 	jwtManager         *auth.JWTManager
@@ -42,22 +46,26 @@ type TokenResponse struct {
 }
 
 func (h *AuthHandler) GetToken(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 
 	var req TokenRequest
 	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
+		middleware.RecordAuthAttempt("invalid_json")
 		utils.RespondError(w, http.StatusBadRequest, "INVALID_JSON", "invalid request body", nil)
 		return
 	}
 
 	// validate shared secret
 	if req.ClientSecret != h.authFingerprintKey {
+		middleware.RecordAuthAttempt("invalid_secret")
+		authLog().Warn("invalid client secret", "remote", r.RemoteAddr)
 		utils.RespondError(w, http.StatusUnauthorized, "INVALID_SECRET", "invalid client secret", nil)
 		return
 	}
 
 	// Return if no fingerprint is found
 	if req.Fingerprint == "" {
+		middleware.RecordAuthAttempt("missing_fingerprint")
 		utils.RespondError(w, http.StatusBadRequest, "MISSING_FINGERPRINT", "fingerprint is required", nil)
 		return
 	}
@@ -67,6 +75,8 @@ func (h *AuthHandler) GetToken(w http.ResponseWriter, r *http.Request) {
 	err := db.Where("ssh_key_fingerprint = ?", req.Fingerprint).First(&user).Error
 	if err == gorm.ErrRecordNotFound {
 		if req.SSHPublicKey == "" {
+			middleware.RecordAuthAttempt("user_not_found")
+			authLog().Warn("user not found and no public key for registration", "fingerprint", req.Fingerprint)
 			utils.RespondError(w, http.StatusUnauthorized, "USER_NOT_FOUND", "no user found for this fingerprint", nil)
 			return
 		}
@@ -75,36 +85,30 @@ func (h *AuthHandler) GetToken(w http.ResponseWriter, r *http.Request) {
 			SSHPublicKey:      req.SSHPublicKey,
 		}
 		if err := db.Create(&user).Error; err != nil {
+			middleware.RecordAuthAttempt("error")
+			authLog().Error("failed to create user", "error", err)
 			utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to create user", nil)
 			return
 		}
+		middleware.RecordAuthAttempt("registered")
+		authLog().Info("user registered", "user_id", user.ID)
 	} else if err != nil {
+		middleware.RecordAuthAttempt("error")
+		authLog().Error("failed to look up user", "error", err)
 		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to look up user", nil)
 		return
 	}
 
-	if req.SSHPublicKey != "" {
-		sshKey := models.SSHKey{
-			UserID:      user.ID,
-			Fingerprint: req.Fingerprint,
-			PublicKey:   req.SSHPublicKey,
-		}
-		if err := db.Where(models.SSHKey{Fingerprint: req.Fingerprint}).FirstOrCreate(&sshKey).Error; err != nil {
-			// we specifically want to block users whos ssh key failed to save. this is to prevent downstream errors which i dont want to deal with now
-			// !TODO add a way to just log the errror and app continue without trying to save carts, cards and addresses. this way the users wouldnt
-			// just be kicked, they would shop normally but on their next login they would need to add all their data again.
-			utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to save ssh key", nil)
-			return
-		}
-	}
-
 	token, err := h.jwtManager.GenerateToken(user.ID, user.Email, user.Name)
 	if err != nil {
+		middleware.RecordAuthAttempt("error")
+		authLog().Error("failed to generate token", "user_id", user.ID, "error", err)
 		utils.RespondError(w, http.StatusInternalServerError, "TOKEN_ERROR", "failed to generate token", nil)
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	middleware.RecordAuthAttempt("success")
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"access_token": token,
 		"token_type":   "Bearer",
 		"expires_in":   1800, // 30 minutes in seconds
@@ -123,7 +127,7 @@ type RegisterRequest struct {
 // RegisterWithSSHKey registers a new user with their SSH public key
 // No username required - following terminal.shop pattern
 func (h *AuthHandler) RegisterWithSSHKey(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 
 	var req RegisterRequest
 	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
@@ -142,7 +146,7 @@ func (h *AuthHandler) RegisterWithSSHKey(w http.ResponseWriter, r *http.Request)
 	}
 
 	if len(errors) > 0 {
-		utils.RespondError(w, http.StatusBadRequest, "VALIDATION_ERROR", "validation failed", map[string]interface{}{
+		utils.RespondError(w, http.StatusBadRequest, "VALIDATION_ERROR", "validation failed", map[string]any{
 			"errors": errors,
 		})
 		return
@@ -169,14 +173,14 @@ func (h *AuthHandler) RegisterWithSSHKey(w http.ResponseWriter, r *http.Request)
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusCreated, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusCreated, map[string]any{
 		"user": user.ToPublic(),
 	})
 }
 
 // GetUserBySSHKey retrieves a user by their SSH key fingerprint
 func (h *AuthHandler) GetUserBySSHKey(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 
 	fingerprint := r.URL.Query().Get("fingerprint")
 	if fingerprint == "" {
@@ -191,7 +195,7 @@ func (h *AuthHandler) GetUserBySSHKey(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"user": user.ToPublic(),
 	})
 }

api/handlers/auth_test.go

@@ -22,7 +22,7 @@ const testClientSecret = "test-client-secret"
 func setupAuthHandlerTestDB(t *testing.T) (string, *auth.JWTManager, *AuthHandler) {
 	t.Helper()
 	testDB := "test_auth.db"
-	os.Remove(testDB)
+	_ = os.Remove(testDB)
 	database.ResetForTesting()
 
 	db, err := database.Connect(testDB)
@@ -62,7 +62,7 @@ func createAuthTestUser(t *testing.T, fingerprint string) models.User {
 
 func TestGetTokenSuccess(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	user := createAuthTestUser(t, "SHA256:testfingerprint123")
@@ -108,7 +108,7 @@ func TestGetTokenSuccess(t *testing.T) {
 
 func TestGetTokenBadSecret(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	body, _ := json.Marshal(map[string]string{
@@ -128,7 +128,7 @@ func TestGetTokenBadSecret(t *testing.T) {
 
 func TestGetTokenMissingFingerprint(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	body, _ := json.Marshal(map[string]string{
@@ -147,7 +147,7 @@ func TestGetTokenMissingFingerprint(t *testing.T) {
 
 func TestGetTokenUnknownFingerprint(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	body, _ := json.Marshal(map[string]string{
@@ -167,7 +167,7 @@ func TestGetTokenUnknownFingerprint(t *testing.T) {
 
 func TestGetTokenInvalidJSON(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	req := httptest.NewRequest("POST", "/api/v1/auth/token", bytes.NewBufferString("{bad json"))
@@ -185,7 +185,7 @@ func TestGetTokenInvalidJSON(t *testing.T) {
 
 func TestRegisterWithSSHKeySuccess(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	body, _ := json.Marshal(map[string]string{
@@ -207,7 +207,7 @@ func TestRegisterWithSSHKeySuccess(t *testing.T) {
 
 func TestRegisterWithSSHKeyDuplicate(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	createAuthTestUser(t, "SHA256:existingfp")
@@ -229,7 +229,7 @@ func TestRegisterWithSSHKeyDuplicate(t *testing.T) {
 
 func TestRegisterWithSSHKeyMissingFields(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	body, _ := json.Marshal(map[string]string{
@@ -250,7 +250,7 @@ func TestRegisterWithSSHKeyMissingFields(t *testing.T) {
 
 func TestGetUserBySSHKeySuccess(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	createAuthTestUser(t, "SHA256:lookupfp")
@@ -267,7 +267,7 @@ func TestGetUserBySSHKeySuccess(t *testing.T) {
 
 func TestGetUserBySSHKeyNotFound(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	req := httptest.NewRequest("GET", "/api/v1/auth/ssh?fingerprint=SHA256:nope", nil)
@@ -282,7 +282,7 @@ func TestGetUserBySSHKeyNotFound(t *testing.T) {
 
 func TestGetUserBySSHKeyMissingParam(t *testing.T) {
 	testDB, _, handler := setupAuthHandlerTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	req := httptest.NewRequest("GET", "/api/v1/auth/ssh", nil)

api/handlers/card_test.go

@@ -0,0 +1,156 @@
+package handlers
+
+import (
+	"encoding/json"
+	"net/http"
+	"net/http/httptest"
+	"os"
+	"strconv"
+	"testing"
+	"time"
+
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+
+	"github.com/go-chi/chi/v5"
+)
+
+// TestGetCards_FiltersExpiredRows drives the SQL WHERE claude used by
+// GetCards. a column-name typo (e.g used_id instead of user_id) surfaces
+// here as a sqlite error, not in prod
+func TestGetCards_FiltersExpiredRows(t *testing.T) {
+	testDB, user := setupCardsExpireTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	now := time.Now()
+	past := now.Add(-1 * time.Hour)
+	future := now.Add(24 * time.Hour)
+
+	expired := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_expired", Last4: "1111",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &past,
+	}
+	fresh := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_fresh", Last4: "2222",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &future,
+	}
+	legacy := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_legacy", Last4: "3333",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030,
+	}
+	for _, card := range []*models.Card{&expired, &fresh, &legacy} {
+		if err := db.Create(card).Error; err != nil {
+			t.Fatalf("seed card: %v", err)
+		}
+	}
+
+	handler := NewCardHandler("")
+	req := authRequest("GET", "/api/v1/cards", nil, user.ID)
+	w := httptest.NewRecorder()
+	handler.GetCards(w, req)
+
+	if w.Code != http.StatusOK {
+		t.Fatalf("GetCards status %d, body %s", w.Code, w.Body.String())
+	}
+
+	var resp struct {
+		Success bool `json:"success"`
+		Data    struct {
+			Cards []models.Card `json:"cards"`
+		} `json:"data"`
+	}
+	if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
+		t.Fatalf("decode: %v", err)
+	}
+	if len(resp.Data.Cards) != 2 {
+		t.Fatalf("want 2 visible cards (fresh + legacy NULL), got %d", len(resp.Data.Cards))
+	}
+	for _, card := range resp.Data.Cards {
+		if card.ID == expired.ID {
+			t.Fatalf("expired card leaked into GetCards response")
+		}
+	}
+}
+
+// TestSetDefaultCard_ExpiredReturns410 verifies the sync-expire branch when
+// the user acts on a card whose retention deadline already elapsed
+func TestSetDefaultCard_ExpiredReturns410(t *testing.T) {
+	testDB, user := setupCardsExpireTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	past := time.Now().Add(-1 * time.Hour)
+	card := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_expired", Last4: "1111",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &past,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+
+	handler := NewCardHandler("")
+	idStr := strconv.FormatUint(uint64(card.ID), 10)
+	req := authRequest("PUT", "/api/v1/cards/"+idStr+"/default", nil, user.ID)
+	routeCtx := chi.NewRouteContext()
+	routeCtx.URLParams.Add("id", idStr)
+	req = req.WithContext(contextWithRoute(req.Context(), routeCtx))
+
+	w := httptest.NewRecorder()
+	handler.SetDefaultCard(w, req)
+
+	if w.Code != http.StatusGone {
+		t.Fatalf("want 410 gone, got %d, body %s", w.Code, w.Body.String())
+	}
+	var resp struct {
+		Error struct {
+			Code string `json:"code"`
+		} `json:"error"`
+	}
+	_ = json.NewDecoder(w.Body).Decode(&resp)
+	if resp.Error.Code != "CARD_STORAGE_EXPIRED" {
+		t.Fatalf("want CARD_STORAGE_EXPIRED code, got %q", resp.Error.Code)
+	}
+
+	var soft models.Card
+	if err := db.Unscoped().First(&soft, card.ID).Error; err != nil {
+		t.Fatalf("reload card unscoped: %v", err)
+	}
+	if !soft.DeletedAt.Valid {
+		t.Fatalf("expired card was not soft-deleted")
+	}
+}
+
+// TestRefreshCardStorageTTL_BumpLastUsedAndExpiry exercises the SQL Updates
+// map used by both the payment_intent.succeede webhook and the duplicate-card
+// add path. Column-name typos in the map surface here
+func TestRefreshCardStorageTTL_BumpLastUsedAndExpiry(t *testing.T) {
+	testDB, user := setupCardsExpireTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	old := time.Now().Add(-30 * 24 * time.Hour)
+	card := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_refresh", Last4: "4242",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &old,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+
+	now := time.Now()
+	if err := refreshCardStorageTTL(db, card.ID, now); err != nil {
+		t.Fatalf("refreshCardStorageTTL: %v", err)
+	}
+
+	var reloaded models.Card
+	if err := db.First(&reloaded, card.ID).Error; err != nil {
+		t.Fatalf("reload card: %v", err)
+	}
+	if reloaded.LastUsedAt == nil || !reloaded.StorageExpiresAt.After(now.Add(179*24*time.Hour)) {
+		t.Fatalf("storage_expires_at not extended, got %v", reloaded.StorageExpiresAt)
+	}
+}

api/handlers/cards.go

@@ -5,9 +5,11 @@ import (
 	"encoding/hex"
 	"encoding/json"
 	"fmt"
+	"log/slog"
 	"net/http"
 	"strconv"
-	"sync"
+	"strings"
+	"time"
 
 	"github.com/go-chi/chi/v5"
 	"github.com/stripe/stripe-go/v78"
@@ -24,64 +26,79 @@ import (
 	stripeSession "github.com/stripe/stripe-go/v78/checkout/session"
 )
 
-// payRedirects maps short tokens to full Stripe checkout URLs.
-var (
-	payRedirects   = map[string]string{}
-	payRedirectsMu sync.Mutex
-)
+const RedirectTTL = 10 * time.Minute
 
-func storeRedirect(stripeURL string) string {
-	b := make([]byte, 4)
-	rand.Read(b)
+func storeRedirect(stripeURL, purpose string) (string, error) {
+	b := make([]byte, 16)
+	if _, err := rand.Read(b); err != nil {
+		return "", err
+	}
 	token := hex.EncodeToString(b)
-	payRedirectsMu.Lock()
-	payRedirects[token] = stripeURL
-	payRedirectsMu.Unlock()
-	return token
+	now := time.Now()
+	rec := models.PayRedirect{
+		Token:     token,
+		URL:       stripeURL,
+		Purpose:   purpose,
+		CreatedAt: now,
+		ExpiresAt: now.Add(RedirectTTL),
+	}
+	if err := database.GetDB().Create(&rec).Error; err != nil {
+		return "", err
+	}
+	return token, nil
 }
 
 // PayRedirect resolves a short token and redirects to the Stripe checkout URL.
 func PayRedirect(w http.ResponseWriter, r *http.Request) {
 	token := chi.URLParam(r, "token")
-	payRedirectsMu.Lock()
-	url, ok := payRedirects[token]
-	payRedirectsMu.Unlock()
-	if !ok {
+	db := database.GetDB().WithContext(r.Context())
+	var rec models.PayRedirect
+	if err := db.Where("token = ?", token).First(&rec).Error; err != nil {
 		http.NotFound(w, r)
 		return
 	}
-	http.Redirect(w, r, url, http.StatusFound)
+	if time.Now().After(rec.ExpiresAt) {
+		db.Where("token = ?", rec.Token).Delete(&models.PayRedirect{})
+		http.NotFound(w, r)
+		return
+	}
+	http.Redirect(w, r, rec.URL, http.StatusFound)
 }
 
 // CardHandler handles saved payment method CRUD.
 type CardHandler struct {
-	stripeKey string
-	appURL    string
+	appURL string
 }
 
-// NewCardHandler creates a new card handler with the Stripe secret key.
-func NewCardHandler(stripeSecretKey string, appURL string) *CardHandler {
-	return &CardHandler{stripeKey: stripeSecretKey, appURL: appURL}
+// NewCardHandler creates a new card handler. Stripe credentials are wired
+// once at startup via stripe.Key in api/main.go.
+func NewCardHandler(appURL string) *CardHandler {
+	return &CardHandler{appURL: appURL}
 }
 
 // GetCards returns all saved cards for the authenticated user.
+// Cards past their retention deadline are filtered out at read time;
+// physical deletion runs in handlers.ReconcileExpiredCards.
 func (h *CardHandler) GetCards(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var cards []models.Card
-	db.Where("user_id = ?", userID).Order("is_default DESC, created_at DESC").Find(&cards)
+	db.Where(
+		"user_id = ? AND (storage_expires_at IS NULL OR storage_expires_at > ?)",
+		userID, time.Now(),
+	).Order("is_default DESC, created_at DESC").Find(&cards)
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"cards": cards,
 	})
 }
 
-// func utils.RespondError(w http.ResponseWriter, statusCode int, code string, message string, details map[string]interface{})
+// func utils.RespondError(w http.ResponseWriter, statusCode int, code string, message string, details map[string]any)
 
 // GetCard returns a single saved card by ID.
 func (h *CardHandler) GetCard(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	idStr := chi.URLParam(r, "id")
@@ -97,13 +114,13 @@ func (h *CardHandler) GetCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"card": card,
 	})
 }
 
 func (h *CardHandler) SetDefaultCard(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	idStr := chi.URLParam(r, "id")
@@ -119,6 +136,15 @@ func (h *CardHandler) SetDefaultCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
+	if card.IsStorageExpired(time.Now()) {
+		if err := expireStoredCard(db, &card); err != nil {
+			utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to expire card", nil)
+			return
+		}
+		respondCardStorageExpired(w)
+		return
+	}
+
 	if err := db.Model(&models.Card{}).Where("user_id = ?", userID).Update("is_default", false).Error; err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to update card", nil)
 		return
@@ -130,13 +156,13 @@ func (h *CardHandler) SetDefaultCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"card": card,
 	})
 }
 
 func (h *CardHandler) CollectCard(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var user models.User
@@ -145,8 +171,6 @@ func (h *CardHandler) CollectCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	stripe.Key = h.stripeKey
-
 	if err := ensureStripeCustomer(db, &user); err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "STRIPE_ERROR", "failed to create stripe customer", nil)
 		return
@@ -166,8 +190,12 @@ func (h *CardHandler) CollectCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	token := storeRedirect(sess.URL)
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	token, err := storeRedirect(sess.URL, models.RedirectPurposeAddCard)
+	if err != nil {
+		utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to generate redirect token", nil)
+		return
+	}
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"url": fmt.Sprintf("%s/pay/%s", h.appURL, token),
 	})
 }
@@ -184,7 +212,7 @@ type SaveCardRequest struct {
 // fingerprint, attaches to the user's Stripe customer, and saves the
 // card metadata locally. No raw card data is stored at any point.
 func (h *CardHandler) SaveCard(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var req SaveCardRequest
@@ -204,8 +232,6 @@ func (h *CardHandler) SaveCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	stripe.Key = h.stripeKey
-
 	// Ensure the user has a Stripe customer, creating one if needed.
 	if err := ensureStripeCustomer(db, &user); err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "STRIPE_ERROR", "failed to create stripe customer", nil)
@@ -248,6 +274,13 @@ func (h *CardHandler) SaveCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
+	// remove existing local card with the same last4 + brand + expiry
+	var existingCard models.Card
+	if err := db.Where("user_id = ? AND last4 = ? AND brand = ? AND exp_month = ? AND exp_year = ?",
+		user.ID, pm.Card.Last4, string(pm.Card.Brand), pm.Card.ExpMonth, pm.Card.ExpYear).First(&existingCard).Error; err == nil {
+		db.Delete(&existingCard)
+	}
+
 	// Persist only the safe card metadata — no raw card data is stored.
 	card := models.Card{
 		UserID:          user.ID,
@@ -265,7 +298,7 @@ func (h *CardHandler) SaveCard(w http.ResponseWriter, r *http.Request) {
 
 	audit.CardAdded(userID, card.ID, card.Brand, card.Last4)
 
-	utils.RespondSuccess(w, http.StatusCreated, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusCreated, map[string]any{
 		"card": card,
 	})
 }
@@ -273,7 +306,7 @@ func (h *CardHandler) SaveCard(w http.ResponseWriter, r *http.Request) {
 // DeleteCard removes a saved card. If the card is currently set on the user's
 // cart, the cart's card selection is cleared.
 func (h *CardHandler) DeleteCard(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	idStr := chi.URLParam(r, "id")
@@ -298,7 +331,6 @@ func (h *CardHandler) DeleteCard(w http.ResponseWriter, r *http.Request) {
 
 	// Detach from Stripe (best-effort; don't block deletion on Stripe errors).
 	if len(card.StripePaymentID) >= 3 && card.StripePaymentID[:3] == "pm_" {
-		stripe.Key = h.stripeKey
 		_, _ = paymentmethod.Detach(card.StripePaymentID, &stripe.PaymentMethodDetachParams{})
 	}
 
@@ -310,11 +342,57 @@ func (h *CardHandler) DeleteCard(w http.ResponseWriter, r *http.Request) {
 
 	audit.CardDeleted(userID, card.ID)
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"message": "card deleted",
 	})
 }
 
+// expireStoredCard removes a card whose retention deadline elapsed.
+// Local state (cart references + card row) is committed atomically;
+// Stripe detach and audit run only after the local commit so retries
+// cannot double-fire the audit event. Stripe detach is gated on
+// stripe.Key being non-empty so tests (which never init the SDK key)
+// skip the real network call without an explicit flag.
+func expireStoredCard(db *gorm.DB, card *models.Card) error {
+	if err := db.Transaction(func(tx *gorm.DB) error {
+		if err := tx.Model(&models.Cart{}).Where("card_id = ? AND user_id = ?", card.ID, card.UserID).Update("card_id", nil).Error; err != nil {
+			return fmt.Errorf("failed to clear expired card from cart: %w", err)
+		}
+		if err := tx.Delete(card).Error; err != nil {
+			return fmt.Errorf("failed to delete expired card: %w", err)
+		}
+		return nil
+	}); err != nil {
+		return err
+	}
+
+	if stripe.Key != "" && strings.HasPrefix(card.StripePaymentID, "pm_") {
+		if _, err := paymentmethod.Detach(card.StripePaymentID, &stripe.PaymentMethodDetachParams{}); err != nil {
+			slog.Warn("failed to detach expired card", "card_id", card.ID, "error", err)
+		}
+	}
+
+	audit.CardExpired(card.UserID, card.ID)
+	return nil
+}
+
+func refreshCardStorageTTL(db *gorm.DB, cardID uint, now time.Time) error {
+	return db.Model(&models.Card{}).Where("id = ?", cardID).Updates(map[string]any{
+		"last_used_at":       now,
+		"storage_expires_at": models.CardStorageExpiresAt(now),
+	}).Error
+}
+
+func respondCardStorageExpired(w http.ResponseWriter) {
+	utils.RespondError(
+		w,
+		http.StatusGone,
+		"CARD_STORAGE_EXPIRED",
+		"saved card expired, add it again",
+		nil,
+	)
+}
+
 // ensureStripeCustomer creates a Stripe Customer for the user if they don't
 // already have one and persists the customer ID. Safe to call concurrently —
 // a duplicate Stripe customer is harmless; the local record reflects the first
@@ -338,7 +416,7 @@ func ensureStripeCustomer(gdb *gorm.DB, user *models.User) error {
 	}
 	user.StripeCustomerID = cust.ID
 	if err := gdb.Save(user).Error; err != nil {
-		return fmt.Errorf("Failed to save stripe customer: %w", err)
+		return fmt.Errorf("failed to save stripe customer: %w", err)
 	}
 	return nil
 }

api/handlers/cards_expire_test.go

@@ -0,0 +1,156 @@
+package handlers
+
+import (
+	"context"
+	"os"
+	"testing"
+	"time"
+
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+)
+
+// TestReconcileExpiredCards_RemovesPastDeadlineOnly drives the real SQL path
+// so a column-name typo in the WHERE clause surfaces here, not in production.
+func TestReconcileExpiredCards_RemovesPastDeadlineOnly(t *testing.T) {
+	testDB, user := setupCardsExpireTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	now := time.Now()
+	past := now.Add(-1 * time.Hour)
+	future := now.Add(24 * time.Hour)
+
+	expired := models.Card{
+		UserID:           user.ID,
+		StripePaymentID:  "tok_expired",
+		Last4:            "1111",
+		Brand:            "Visa",
+		ExpMonth:         1,
+		ExpYear:          2030,
+		StorageExpiresAt: &past,
+	}
+	fresh := models.Card{
+		UserID:           user.ID,
+		StripePaymentID:  "tok_fresh",
+		Last4:            "2222",
+		Brand:            "Visa",
+		ExpMonth:         1,
+		ExpYear:          2030,
+		StorageExpiresAt: &future,
+	}
+	noTTL := models.Card{
+		UserID:          user.ID,
+		StripePaymentID: "tok_legacy",
+		Last4:           "3333",
+		Brand:           "Visa",
+		ExpMonth:        1,
+		ExpYear:         2030,
+	}
+	for _, c := range []*models.Card{&expired, &fresh, &noTTL} {
+		if err := db.Create(c).Error; err != nil {
+			t.Fatalf("seed card: %v", err)
+		}
+	}
+
+	cart := models.Cart{UserID: user.ID, CardID: &expired.ID}
+	if err := db.Create(&cart).Error; err != nil {
+		t.Fatalf("seed cart: %v", err)
+	}
+
+	ReconcileExpiredCards(context.Background())
+
+	var remaining []models.Card
+	if err := db.Where("user_id = ?", user.ID).Find(&remaining).Error; err != nil {
+		t.Fatalf("list cards: %v", err)
+	}
+	if len(remaining) != 2 {
+		t.Fatalf("want 2 cards remaining, got %d", len(remaining))
+	}
+	for _, c := range remaining {
+		if c.ID == expired.ID {
+			t.Fatalf("expired card was not deleted")
+		}
+	}
+
+	var refreshed models.Cart
+	if err := db.First(&refreshed, cart.ID).Error; err != nil {
+		t.Fatalf("reload cart: %v", err)
+	}
+	if refreshed.CardID != nil {
+		t.Fatalf("cart still references expired card: %v", refreshed.CardID)
+	}
+}
+
+// TestReconcileExpiredCards_SweepsAcrossUsers verifies the sweeper is not
+// scoped to one user; it must collect every past-deadline row in one pass.
+func TestReconcileExpiredCards_SweepsAcrossUsers(t *testing.T) {
+	testDB, user := setupCardsExpireTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	past := time.Now().Add(-1 * time.Hour)
+
+	other := models.User{
+		SSHKeyFingerprint: "SHA256:other",
+		SSHPublicKey:      "ssh-ed25519 AAAA other",
+		Name:              "Other",
+		Email:             "other@example.com",
+	}
+	if err := db.Create(&other).Error; err != nil {
+		t.Fatalf("seed other user: %v", err)
+	}
+
+	for _, uid := range []uint{user.ID, other.ID} {
+		c := models.Card{
+			UserID:           uid,
+			StripePaymentID:  "tok_expired",
+			Last4:            "9999",
+			Brand:            "Visa",
+			ExpMonth:         1,
+			ExpYear:          2030,
+			StorageExpiresAt: &past,
+		}
+		if err := db.Create(&c).Error; err != nil {
+			t.Fatalf("seed card: %v", err)
+		}
+	}
+
+	ReconcileExpiredCards(context.Background())
+
+	var count int64
+	if err := db.Model(&models.Card{}).Count(&count).Error; err != nil {
+		t.Fatalf("count cards: %v", err)
+	}
+	if count != 0 {
+		t.Fatalf("want 0 cards after sweep, got %d", count)
+	}
+}
+
+func setupCardsExpireTestDB(t *testing.T) (string, models.User) {
+	t.Helper()
+	testDB := "test_cards_expire.db"
+	_ = os.Remove(testDB)
+	database.ResetForTesting()
+
+	db, err := database.Connect(testDB)
+	if err != nil {
+		t.Fatalf("connect: %v", err)
+	}
+	if err := database.Migrate(db); err != nil {
+		t.Fatalf("migrate: %v", err)
+	}
+
+	user := models.User{
+		SSHKeyFingerprint: "SHA256:cards-expire",
+		SSHPublicKey:      "ssh-ed25519 AAAA cardsexpire",
+		Name:              "Test User",
+		Email:             "cards-expire@example.com",
+	}
+	if err := db.Create(&user).Error; err != nil {
+		t.Fatalf("seed user: %v", err)
+	}
+	return testDB, user
+}

api/handlers/cart.go

@@ -1,34 +1,49 @@
 package handlers
 
 import (
+	"context"
 	"encoding/json"
 	"fmt"
 	"net/http"
+	"strconv"
+	"time"
 
+	"github.com/go-chi/chi/v5"
 	"github.com/stripe/stripe-go/v78"
 	"github.com/stripe/stripe-go/v78/paymentintent"
 	"github.com/stripe/stripe-go/v78/paymentmethod"
 	"gorm.io/gorm"
 
+	"go.opentelemetry.io/otel"
+
 	"terminalShop/api/middleware"
 	"terminalShop/pkg/audit"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
+	"terminalShop/pkg/notify"
 	"terminalShop/pkg/utils"
 )
 
 type CartHandler struct {
-	stripeKey string
+	appURL        string
+	maxOrderCents int
 }
 
-// NewCartHandler creates a new cart handler with the Stripe secret key
-func NewCartHandler(stripeSecretKey string) *CartHandler {
-	return &CartHandler{stripeKey: stripeSecretKey}
+// maxAuthIssuances caps how many times a single ordes's PaymentIntent can be
+// pushed into requires_action; one initial challende plus up to three retries
+// before we tell the customer to use a different card. Counted via existing
+// audit rows (audit.EventOrderRequiresAction) so the cap stays migration-free.
+const maxAuthIssuances = 4
+
+// NewCartHandler creates a new cart handler. Stripe credentials are wired
+// once at startup via stripe.Key in api/main.go.
+func NewCartHandler(appURL string, maxOrderCents int) *CartHandler {
+	return &CartHandler{appURL: appURL, maxOrderCents: maxOrderCents}
 }
 
 // getOrCreateCart finds the users cart or creates one.
-func getOrCreateCart(userID uint) (*models.Cart, error) {
-	db := database.GetDB()
+func getOrCreateCart(ctx context.Context, userID uint) (*models.Cart, error) {
+	db := database.GetDB().WithContext(ctx)
 	var cart models.Cart
 	err := db.Where("user_id = ?", userID).First(&cart).Error
 	if err != nil {
@@ -40,18 +55,18 @@ func getOrCreateCart(userID uint) (*models.Cart, error) {
 	return &cart, nil
 }
 
-func cartResponse(cart *models.Cart) map[string]interface{} {
-	db := database.GetDB()
+func cartResponse(ctx context.Context, cart *models.Cart) map[string]any {
+	db := database.GetDB().WithContext(ctx)
 
 	var items []models.CartItem
 	db.Where("cart_id = ? AND quantity > 0", cart.ID).Preload("Coffee").Find(&items)
 
 	subtotal := 0
-	itemsData := make([]map[string]interface{}, 0, len(items))
+	itemsData := make([]map[string]any, 0, len(items))
 	for _, item := range items {
 		lineTotal := item.Coffee.Price * item.Quantity
 		subtotal += lineTotal
-		itemsData = append(itemsData, map[string]interface{}{
+		itemsData = append(itemsData, map[string]any{
 			"id":        item.ID,
 			"coffee_id": item.CoffeeID,
 			"quantity":  item.Quantity,
@@ -60,7 +75,7 @@ func cartResponse(cart *models.Cart) map[string]interface{} {
 		})
 	}
 
-	return map[string]interface{}{
+	return map[string]any{
 		"items":            itemsData,
 		"subtotal":         subtotal,
 		"address_id":       cart.AddressID,
@@ -73,14 +88,14 @@ func cartResponse(cart *models.Cart) map[string]interface{} {
 func (h *CartHandler) GetCart(w http.ResponseWriter, r *http.Request) {
 	userID := middleware.UserIDFromContext(r.Context())
 
-	cart, err := getOrCreateCart(userID)
+	cart, err := getOrCreateCart(r.Context(), userID)
 	if err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "CART_ERROR", "failed to get cart", nil)
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
-		"cart": cartResponse(cart),
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
+		"cart": cartResponse(r.Context(), cart),
 	})
 }
 
@@ -90,7 +105,7 @@ type SetItemRequest struct {
 }
 
 func (h *CartHandler) SetItem(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var req SetItemRequest
@@ -110,7 +125,7 @@ func (h *CartHandler) SetItem(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	cart, err := getOrCreateCart(userID)
+	cart, err := getOrCreateCart(r.Context(), userID)
 	if err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "CART_ERROR", "failed to get cart", nil)
 		return
@@ -142,8 +157,8 @@ func (h *CartHandler) SetItem(w http.ResponseWriter, r *http.Request) {
 		}
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
-		"cart": cartResponse(cart),
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
+		"cart": cartResponse(r.Context(), cart),
 	})
 }
 
@@ -152,7 +167,7 @@ type SetAddressRequest struct {
 }
 
 func (h *CartHandler) SetAddress(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var req SetAddressRequest
@@ -167,7 +182,7 @@ func (h *CartHandler) SetAddress(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	cart, err := getOrCreateCart(userID)
+	cart, err := getOrCreateCart(r.Context(), userID)
 	if err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "CART_ERROR", "failed to get cart", nil)
 		return
@@ -178,7 +193,7 @@ func (h *CartHandler) SetAddress(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"message": "address set",
 	})
 }
@@ -188,7 +203,7 @@ type SetCardRequest struct {
 }
 
 func (h *CartHandler) SetCard(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var req SetCardRequest
@@ -203,7 +218,16 @@ func (h *CartHandler) SetCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	cart, err := getOrCreateCart(userID)
+	if card.IsStorageExpired(time.Now()) {
+		if err := expireStoredCard(db, &card); err != nil {
+			utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to expire card", nil)
+			return
+		}
+		respondCardStorageExpired(w)
+		return
+	}
+
+	cart, err := getOrCreateCart(r.Context(), userID)
 	if err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "CART_ERROR", "failed to get cart", nil)
 		return
@@ -214,16 +238,16 @@ func (h *CartHandler) SetCard(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"message": "card set",
 	})
 }
 
 func (h *CartHandler) ClearCart(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
-	cart, err := getOrCreateCart(userID)
+	cart, err := getOrCreateCart(r.Context(), userID)
 	if err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "CART_ERROR", "failed to get cart", nil)
 		return
@@ -234,17 +258,22 @@ func (h *CartHandler) ClearCart(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"message": "cart cleared",
 	})
 }
 
 func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
-	cart, err := getOrCreateCart(userID)
+	ctx, span := otel.Tracer("api").Start(r.Context(), "cart.convert")
+	defer span.End()
+	r = r.WithContext(ctx)
+
+	cart, err := getOrCreateCart(r.Context(), userID)
 	if err != nil {
+		middleware.RecordCartConversion("cart_lookup_failed")
 		utils.RespondError(w, http.StatusInternalServerError, "CART_ERROR", "failed to get cart", nil)
 		return
 	}
@@ -253,42 +282,57 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 	db.Where("cart_id = ? AND quantity > 0", cart.ID).Preload("Coffee").Find(&items)
 
 	if len(items) == 0 {
+		middleware.RecordCartConversion("validation_empty_cart")
 		utils.RespondError(w, http.StatusBadRequest, "VALIDATION_ERROR", "cart is empty", nil)
 		return
 	}
 
 	if cart.AddressID == nil {
+		middleware.RecordCartConversion("validation_missing_address")
 		utils.RespondError(w, http.StatusBadRequest, "VALIDATION_ERROR", "shipping address is required", nil)
 		return
 	}
 
 	if cart.CardID == nil {
+		middleware.RecordCartConversion("validation_missing_card")
 		utils.RespondError(w, http.StatusBadRequest, "VALIDATION_ERROR", "payment card is required", nil)
 		return
 	}
 
 	var address models.Address
 	if err := db.First(&address, *cart.AddressID).Error; err != nil {
+		middleware.RecordCartConversion("validation_invalid_address")
 		utils.RespondError(w, http.StatusBadRequest, "INVALID_ADDRESS", "shipping address not found", nil)
 		return
 	}
 
 	var card models.Card
 	if err := db.First(&card, *cart.CardID).Error; err != nil {
+		middleware.RecordCartConversion("validation_invalid_card")
 		utils.RespondError(w, http.StatusBadRequest, "INVALID_CARD", "payment card not found", nil)
 		return
 	}
 
+	if card.IsStorageExpired(time.Now()) {
+		middleware.RecordCartConversion("validation_card_expired")
+		if err := expireStoredCard(db, &card); err != nil {
+			utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to expire card", nil)
+			return
+		}
+		respondCardStorageExpired(w)
+		return
+	}
+
 	var user models.User
 	if err := db.First(&user, userID).Error; err != nil {
+		middleware.RecordCartConversion("user_not_found")
 		utils.RespondError(w, http.StatusNotFound, "USER_NOT_FOUND", "user not found", nil)
 		return
 	}
 
-	stripe.Key = h.stripeKey
-
 	// Ensure the user has a Stripe customer (shared helper with cards handler).
 	if err := ensureStripeCustomer(db, &user); err != nil {
+		middleware.RecordCartConversion("stripe_customer_failed")
 		utils.RespondError(w, http.StatusInternalServerError, "STRIPE_ERROR", "failed to create stripe customer", nil)
 		return
 	}
@@ -336,7 +380,20 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 
 	total := subtotal + cart.ShippingCost
 
+	if h.maxOrderCents > 0 && total > h.maxOrderCents {
+		middleware.RecordCartConversion("validation_over_limit")
+		audit.CartRejected(userID, total, h.maxOrderCents)
+		utils.RespondError(w, http.StatusBadRequest, "CART_OVER_LIMIT",
+			fmt.Sprintf("order total must be at most $%.2f", float64(h.maxOrderCents)/100),
+			map[string]any{
+				"total_cents": total,
+				"limit_cents": h.maxOrderCents,
+			})
+		return
+	}
+
 	if total < 50 {
+		middleware.RecordCartConversion("validation_min_amount")
 		utils.RespondError(w, http.StatusBadRequest, "VALIDATION_ERROR", "order total must be at least $0.50", nil)
 		return
 	}
@@ -363,6 +420,7 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 	}
 
 	if err := db.Create(&order).Error; err != nil {
+		middleware.RecordCartConversion("db_create_order_failed")
 		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to create order", nil)
 		return
 	}
@@ -372,16 +430,15 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 	// Charge the card. The idempotency key is tied to the order ID so retries
 	// never produce a double charge.
 	piParams := &stripe.PaymentIntentParams{
-		Amount:        stripe.Int64(int64(total)),
-		Currency:      stripe.String(string(stripe.CurrencyUSD)),
-		Customer:      stripe.String(user.StripeCustomerID),
-		PaymentMethod: stripe.String(paymentMethodID),
-		AutomaticPaymentMethods: &stripe.PaymentIntentAutomaticPaymentMethodsParams{
-			Enabled:        stripe.Bool(true),
-			AllowRedirects: stripe.String("never"),
-		},
-		Confirm:     stripe.Bool(true),
-		Description: stripe.String(fmt.Sprintf("terminal.shop order #%d", order.ID)),
+		Amount:             stripe.Int64(int64(total)),
+		Currency:           stripe.String(string(stripe.CurrencyUSD)),
+		Customer:           stripe.String(user.StripeCustomerID),
+		PaymentMethod:      stripe.String(paymentMethodID),
+		OffSession:         stripe.Bool(true),
+		PaymentMethodTypes: stripe.StringSlice([]string{"card"}),
+		ReturnURL:          stripe.String(h.appURL + "/post-3ds"),
+		Confirm:            stripe.Bool(true),
+		Description:        stripe.String(fmt.Sprintf("terminal.shop order #%d", order.ID)),
 		Shipping: &stripe.ShippingDetailsParams{
 			Name: stripe.String(address.Name),
 			Address: &stripe.AddressParams{
@@ -399,27 +456,45 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 		"order_id": fmt.Sprintf("%d", order.ID),
 	}
 
+	stripeStart := time.Now()
 	pi, err := paymentintent.New(piParams)
+	stripeDur := time.Since(stripeStart).Seconds()
 	if err != nil {
-		db.Model(&order).Update("status", models.OrderStatusFailed)
+		middleware.ObserveStripeRequest("payment_intent_create", "error", stripeDur)
 		if stripeErr, ok := err.(*stripe.Error); ok {
+			if stripeErr.Code == stripe.ErrorCodeAuthenticationRequired && stripeErr.PaymentIntent != nil {
+				h.respondRequiresAction(w, &order, paymentMethodID, stripeErr.PaymentIntent)
+				return
+			}
+			db.Model(&order).Update("status", models.OrderStatusFailed)
 			switch stripeErr.Type {
 			case stripe.ErrorTypeCard:
+				middleware.RecordCartConversion("card_declined")
 				audit.OrderFailed(userID, order.ID, total, stripeErr.Msg)
-				utils.RespondError(w, http.StatusPaymentRequired, "CARD_DECLINED", stripeErr.Msg, nil)
+				utils.RespondError(w, http.StatusPaymentRequired, mapStripeCardErrCode(stripeErr.Code), stripeErr.Msg, nil)
 			case stripe.ErrorTypeInvalidRequest:
+				middleware.RecordCartConversion("stripe_invalid_request")
 				audit.OrderFailed(userID, order.ID, total, stripeErr.Msg)
 				utils.RespondError(w, http.StatusBadRequest, "INVALID_PAYMENT", stripeErr.Msg, nil)
 			default:
+				middleware.RecordCartConversion("stripe_error")
 				audit.OrderFailed(userID, order.ID, total, stripeErr.Error())
 				utils.RespondError(w, http.StatusInternalServerError, "PAYMENT_FAILED", "payment failed", nil)
 			}
 			return
 		}
+		db.Model(&order).Update("status", models.OrderStatusFailed)
+		middleware.RecordCartConversion("stripe_error")
 		audit.OrderFailed(userID, order.ID, total, err.Error())
 		utils.RespondError(w, http.StatusInternalServerError, "PAYMENT_FAILED", "payment failed", nil)
 		return
 	}
+	middleware.ObserveStripeRequest("payment_intent_create", "success", stripeDur)
+
+	if pi.Status == stripe.PaymentIntentStatusRequiresAction {
+		h.respondRequiresAction(w, &order, paymentMethodID, pi)
+		return
+	}
 
 	// Commit payment ID and clear cart in a single transaction.
 	txErr := db.Transaction(func(tx *gorm.DB) error {
@@ -431,7 +506,7 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 		if err := tx.Where("cart_id = ?", cart.ID).Delete(&models.CartItem{}).Error; err != nil {
 			return err
 		}
-		return tx.Model(cart).Updates(map[string]interface{}{
+		return tx.Model(cart).Updates(map[string]any{
 			"address_id": nil,
 			"card_id":    nil,
 		}).Error
@@ -441,19 +516,265 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 		// most dangerous failure mode: the customer paid but has no order.
 		// The reconciliation job will catch this within 5 minutes.
 		// The audit log entry below must be treated as a critical alert.
+		middleware.RecordCartConversion("payment_critical")
 		audit.PaymentCritical(order.ID, pi.ID, txErr)
 		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "payment succeeded but failed to record order — please contact support", nil)
 		return
 	}
 
 	audit.OrderPaid(userID, order.ID, total, pi.ID)
+	middleware.RecordOrderCreated(string(order.Status))
+	middleware.RecordCartConversion("success")
+	middleware.ObserveOrderValueCents(total)
 
 	if err := db.Preload("Items").First(&order, order.ID).Error; err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to preload items", nil)
 		return
 	}
+	go notify.SlackOrderPaid(&order)
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"order": order,
 	})
 }
+
+// respondRequiresAction handles a PaymentIntent that needs 3DS auth. The order
+// transitions to requires_action (see caveat #20 in sca-psd2-compliance.md);
+// the payment_intent.succeeded webhook flips it to paid once the customer
+// completes the bank-hosted challenge. The TUI polls /api/v1/orders/{id}/status.
+func (h *CartHandler) respondRequiresAction(w http.ResponseWriter, order *models.Order, paymentMethodID string, pi *stripe.PaymentIntent) {
+	db := database.GetDB()
+
+	// After an off-session authentication_required decline, the PI sits in
+	// status=requires_payment_method with payment_method detached. Re-confirm
+	// on-session with the same PM so Stripe pushes the PI into requires_action
+	// and populates next_action.redirect_to_url with the 3DS challenge URL.
+	if pi.NextAction == nil || pi.NextAction.RedirectToURL == nil || pi.NextAction.RedirectToURL.URL == "" {
+		confirmed, cerr := paymentintent.Confirm(pi.ID, &stripe.PaymentIntentConfirmParams{
+			PaymentMethod: stripe.String(paymentMethodID),
+			OffSession:    stripe.Bool(false),
+			ReturnURL:     stripe.String(h.appURL + "/post-3ds"),
+		})
+		if cerr == nil && confirmed != nil {
+			pi = confirmed
+		}
+	}
+
+	if pi.NextAction == nil || pi.NextAction.RedirectToURL == nil || pi.NextAction.RedirectToURL.URL == "" {
+		middleware.RecordCartConversion("sca_missing_next_action")
+		db.Model(order).Update("status", models.OrderStatusFailed)
+		audit.OrderFailed(order.UserID, order.ID, order.Total, "stripe returned requires_action without redirect url")
+		utils.RespondError(w, http.StatusBadGateway, "PAYMENT_FAILED", "stripe did not return a 3ds url", nil)
+		return
+	}
+
+	// Persist the paymentIntent id AND set status to requires_action so list
+	// UIs can distinguish "charging" from "awaiting customer 3DS". The
+	// payment_intent.payment_failed webhook from the initial off-session
+	// decline often arrives before this response and flips the order to
+	// failed - override it back so the 3DS-in-flight order shows the
+	// correct state
+	if err := db.Model(order).Updates(map[string]any{
+		"stripe_payment_id": pi.ID,
+		"status":            models.OrderStatusRequiresAction,
+	}).Error; err != nil {
+		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to save payment id", nil)
+		return
+	}
+
+	token, err := storeRedirect(pi.NextAction.RedirectToURL.URL, models.RedirectPurposeCheckout3DS)
+	if err != nil {
+		utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to allocate redirect token", nil)
+		return
+	}
+
+	middleware.RecordCartConversion("requires_action")
+	audit.OrderRequiresAction(order.UserID, order.ID, pi.ID)
+
+	utils.RespondSuccess(w, http.StatusAccepted, map[string]any{
+		"order_id":          order.ID,
+		"payment_intent_id": pi.ID,
+		"status":            "requires_action",
+		"redirect_token":    token,
+		"redirect_url":      fmt.Sprintf("%s/pay/%s", h.appURL, token),
+	})
+}
+
+func mapStripeCardErrCode(code stripe.ErrorCode) string {
+	switch code {
+	case stripe.ErrorCodeAuthenticationRequired:
+		return "AUTHENTICATION_REQUIRED"
+	case "authentication_not_supported":
+		return "AUTHENTICATION_NOT_SUPPORTED"
+	case "card_declined", "":
+		return "CARD_DECLINED"
+	case "expired_card":
+		return "CARD_EXPIRED"
+	case "incorrect_cvc":
+		return "CARD_CVC_FAILED"
+	case "insufficient_funds":
+		return "CARD_INSUFFICIENT_FUNDS"
+	case "processing_error":
+		return "CARD_PROCESSING_ERROR"
+	}
+	return "CARD_DECLINED"
+}
+
+//nolint:unused // wired into Convert cart later
+func appURLForHandler(r *http.Request) string {
+	scheme := "http"
+	if r.TLS != nil || r.Header.Get("X-Forwarded-Proto") == "https" {
+		scheme = "https"
+	}
+	host := r.Host
+	if fh := r.Header.Get("X-Forwarded-Host"); fh != "" {
+		host = fh
+	}
+	return fmt.Sprintf("%s://%s", scheme, host)
+}
+
+// RetryAuth re-Confirms an in-flight PaymentIntent that the customer failed
+// or abandoned during the 3DS challenge, recovering the existing order rather
+// than starting a new checkout. Bound to POST /api/v1/orders/{id}/retry-auth.
+//
+// Stripe's PI state machine bounces back to requires_payment_method after a
+// failed or abandoned 3DS, so paymentintent.Confirm(pi.id, …) mints a fresh
+// next_action.redirect_to_url — the same shape respondRequiresAction already
+// handles. No idempotency key is set: Confirm mutates an existing PI and
+// Stripe collapses by id (see sca-psd2-compliance.md caveat #5).
+func (h *CartHandler) RetryAuth(w http.ResponseWriter, r *http.Request) {
+	db := database.GetDB().WithContext(r.Context())
+	userID := middleware.UserIDFromContext(r.Context())
+
+	idStr := chi.URLParam(r, "id")
+	id64, err := strconv.ParseUint(idStr, 10, 32)
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_ID", "invalid order id", nil)
+		return
+	}
+	orderID := uint(id64)
+
+	var order models.Order
+	if err := db.Where("id = ? AND user_id = ?", orderID, userID).First(&order).Error; err != nil {
+		utils.RespondError(w, http.StatusNotFound, "ORDER_NOT_FOUND", "order not found", nil)
+		return
+	}
+
+	// Retryable source states:
+	//	pending 		- initial attempt mid-flight (pre-PI confirm page)
+	//	requires_action - customer abandoned or failed the 3DS challenge
+	//	failed 			- webhook flipped after a non-recoverable error
+	// terminal states (paid, shipped, delivered, cancelled, refunded) refuse.
+	if order.Status != models.OrderStatusPending &&
+		order.Status != models.OrderStatusRequiresAction &&
+		order.Status != models.OrderStatusFailed {
+		utils.RespondError(w, http.StatusConflict, "INVALID_STATE", "order is already finalized", nil)
+		return
+	}
+	if order.StripePaymentID == "" {
+		utils.RespondError(w, http.StatusConflict, "INVALID_STATE", "order has no payment intent to retry", nil)
+		return
+	}
+
+	// Cap is best-effort: two concurrent retries at issuances=cap-1 will both
+	// pass this check and both Confirm before either writes a new event row.
+	// Per-user RateLimitByUser(10/min) on the route bounds the worst case.
+	// SQLite-WAL has no SELECT ... FOR UPDATE, so a stricter guard would need
+	// a serializing INSERT - not worth the cimplexity at current traffic.
+	var issuances int64
+	if err := db.Model(&models.OrderEvent{}).
+		Where("order_id = ? AND type = ?", order.ID, audit.EventOrderRequiresAction).
+		Count(&issuances).Error; err != nil {
+		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to count auth attempts", nil)
+		return
+	}
+	if issuances >= maxAuthIssuances {
+		middleware.RecordCartConversion("retry_max_attempts")
+		utils.RespondError(w, http.StatusTooManyRequests, "RETRY_LIMIT", "too many authentication attempts, please use a different card", nil)
+		return
+	}
+
+	// scoped card lookup - match the initial-flow policy in ConvertCart so a
+	// card the user deleted (or that the storage-TTL reconciler removed)
+	// cannot be silently re-charged through retry. The ownership clause is
+	// defensive: order.CardID is enforced at SetCard time today but binding
+	// the retry path to that invariant explicitly costs nothing.
+	var card models.Card
+	if err := db.Where("id = ? AND user_id = ?", order.CardID, userID).First(&card).Error; err != nil {
+		utils.RespondError(w, http.StatusConflict, "CARD_NO_LONGER_AVAILABLE", "saved card is no longer available, add it again to retry", nil)
+		return
+	}
+	if card.IsStorageExpired(time.Now()) {
+		if err := expireStoredCard(db, &card); err != nil {
+			utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to expire card", nil)
+			return
+		}
+		respondCardStorageExpired(w)
+		return
+	}
+
+	stripeStart := time.Now()
+	confirmed, cerr := paymentintent.Confirm(order.StripePaymentID, &stripe.PaymentIntentConfirmParams{
+		PaymentMethod: stripe.String(card.StripePaymentID),
+		OffSession:    stripe.Bool(false),
+		ReturnURL:     stripe.String(h.appURL + "/post-3ds"),
+	})
+	stripeDur := time.Since(stripeStart).Seconds()
+	if cerr != nil {
+		middleware.ObserveStripeRequest("payment_intent_confirm", "error", stripeDur)
+		if stripeErr, ok := cerr.(*stripe.Error); ok && stripeErr.Type == stripe.ErrorTypeCard {
+			db.Model(&order).Update("status", models.OrderStatusFailed)
+			audit.OrderFailed(userID, order.ID, order.Total, stripeErr.Msg)
+			middleware.RecordCartConversion("retry_card_declined")
+			utils.RespondError(w, http.StatusPaymentRequired, mapStripeCardErrCode(stripeErr.Code), stripeErr.Msg, nil)
+			return
+		}
+		if stripeErr, ok := cerr.(*stripe.Error); ok && stripeErr.Code == "payment_intent_unexpected_state" {
+			actual, gerr := paymentintent.Get(order.StripePaymentID, nil)
+			if gerr != nil {
+				middleware.RecordCartConversion("retry_stripe_error")
+				utils.RespondError(w, http.StatusBadGateway, "PAYMENT_FAILED", "payment failed", nil)
+				return
+			}
+			switch actual.Status {
+			case stripe.PaymentIntentStatusSucceeded:
+				middleware.RecordCartConversion("retry_race_already_done")
+				utils.RespondSuccess(w, http.StatusAccepted, map[string]any{
+					"order_id": order.ID,
+					"status":   "succeeded",
+				})
+				return
+			case stripe.PaymentIntentStatusCanceled:
+				db.Model(&order).Update("status", models.OrderStatusFailed)
+				audit.OrderFailed(userID, order.ID, order.Total, "payment intent canceled")
+				middleware.RecordCartConversion("retry_pi_canceled")
+				utils.RespondError(w, http.StatusConflict, "INVALID_STATE", "payment intent is canceled, please start a new order", nil)
+				return
+			default:
+				middleware.RecordCartConversion("retry_pi_unexpected_state")
+				utils.RespondError(w, http.StatusBadGateway, "PAYMENT_FAILED", "payment intent in unexpected state", nil)
+				return
+			}
+		}
+
+		middleware.RecordCartConversion("retry_stripe_error")
+		utils.RespondError(w, http.StatusBadGateway, "PAYMENT_FAILED", "payment failed", nil)
+		return
+	}
+	middleware.ObserveStripeRequest("payment_intent_confirm", "success", stripeDur)
+
+	// frictionless 3DS on retry, stripe approved without a new challenge.
+	// the payment_intent.succeeded webhook owns the order.status=paid
+	// transition (matches the initial-flow contract); tell the TUI to keep
+	// polling /orders/{id}/status until it lands
+	if confirmed.Status == stripe.PaymentIntentStatusSucceeded {
+		middleware.RecordCartConversion("retry_frictionless")
+		utils.RespondSuccess(w, http.StatusAccepted, map[string]any{
+			"order_id": order.ID,
+			"status":   "succeeded",
+		})
+		return
+	}
+
+	h.respondRequiresAction(w, &order, card.StripePaymentID, confirmed)
+}

api/handlers/cart_test.go

@@ -3,14 +3,19 @@ package handlers
 import (
 	"bytes"
 	"encoding/json"
+	"fmt"
+	"log/slog"
 	"net/http"
 	"net/http/httptest"
 	"os"
 	"testing"
+	"time"
 
 	"github.com/go-chi/chi/v5"
+	"github.com/stripe/stripe-go/v78"
 
 	"terminalShop/api/middleware"
+	"terminalShop/pkg/audit"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
 )
@@ -20,7 +25,7 @@ import (
 func setupCartTestDB(t *testing.T) (string, models.User) {
 	t.Helper()
 	testDB := "test_cart.db"
-	os.Remove(testDB)
+	_ = os.Remove(testDB)
 	database.ResetForTesting()
 
 	db, err := database.Connect(testDB)
@@ -62,10 +67,10 @@ func authRequest(method, url string, body []byte, userID uint) *http.Request {
 
 func TestGetCartEmpty(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	req := authRequest("GET", "/api/v1/cart", nil, user.ID)
 	w := httptest.NewRecorder()
@@ -80,8 +85,8 @@ func TestGetCartEmpty(t *testing.T) {
 		Success bool `json:"success"`
 		Data    struct {
 			Cart struct {
-				Items    []interface{} `json:"items"`
-				Subtotal int           `json:"subtotal"`
+				Items    []any `json:"items"`
+				Subtotal int   `json:"subtotal"`
 			} `json:"cart"`
 		} `json:"data"`
 	}
@@ -101,13 +106,13 @@ func TestGetCartEmpty(t *testing.T) {
 
 func TestSetItemAndGetCart(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	// Add item (CoffeeID=1, Quantity=2)
-	body, _ := json.Marshal(map[string]interface{}{
+	body, _ := json.Marshal(map[string]any{
 		"coffee_id": 1,
 		"quantity":  2,
 	})
@@ -157,19 +162,19 @@ func TestSetItemAndGetCart(t *testing.T) {
 
 func TestSetItemUpdateQuantity(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	// Add item
-	body, _ := json.Marshal(map[string]interface{}{"coffee_id": 1, "quantity": 2})
+	body, _ := json.Marshal(map[string]any{"coffee_id": 1, "quantity": 2})
 	req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetItem(w, req)
 
 	// Update quantity
-	body, _ = json.Marshal(map[string]interface{}{"coffee_id": 1, "quantity": 5})
+	body, _ = json.Marshal(map[string]any{"coffee_id": 1, "quantity": 5})
 	req = authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w = httptest.NewRecorder()
 	handler.SetItem(w, req)
@@ -190,7 +195,7 @@ func TestSetItemUpdateQuantity(t *testing.T) {
 			} `json:"cart"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if len(resp.Data.Cart.Items) != 1 {
 		t.Fatalf("Expected 1 item after update, got %d", len(resp.Data.Cart.Items))
@@ -202,19 +207,19 @@ func TestSetItemUpdateQuantity(t *testing.T) {
 
 func TestSetItemRemove(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	// Add item
-	body, _ := json.Marshal(map[string]interface{}{"coffee_id": 1, "quantity": 3})
+	body, _ := json.Marshal(map[string]any{"coffee_id": 1, "quantity": 3})
 	req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetItem(w, req)
 
 	// Remove item (quantity 0)
-	body, _ = json.Marshal(map[string]interface{}{"coffee_id": 1, "quantity": 0})
+	body, _ = json.Marshal(map[string]any{"coffee_id": 1, "quantity": 0})
 	req = authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w = httptest.NewRecorder()
 	handler.SetItem(w, req)
@@ -228,11 +233,11 @@ func TestSetItemRemove(t *testing.T) {
 		Success bool `json:"success"`
 		Data    struct {
 			Cart struct {
-				Items []interface{} `json:"items"`
+				Items []any `json:"items"`
 			} `json:"cart"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if len(resp.Data.Cart.Items) != 0 {
 		t.Errorf("Expected 0 items after removal, got %d", len(resp.Data.Cart.Items))
@@ -241,12 +246,12 @@ func TestSetItemRemove(t *testing.T) {
 
 func TestSetItemInvalidProduct(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
-	body, _ := json.Marshal(map[string]interface{}{"coffee_id": 999, "quantity": 1})
+	body, _ := json.Marshal(map[string]any{"coffee_id": 999, "quantity": 1})
 	req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetItem(w, req)
@@ -258,12 +263,12 @@ func TestSetItemInvalidProduct(t *testing.T) {
 
 func TestSetItemMissingCoffeeID(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
-	body, _ := json.Marshal(map[string]interface{}{"quantity": 1})
+	body, _ := json.Marshal(map[string]any{"quantity": 1})
 	req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetItem(w, req)
@@ -275,14 +280,14 @@ func TestSetItemMissingCoffeeID(t *testing.T) {
 
 func TestClearCart(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	// Add two items
 	for _, coffeeID := range []uint{1, 2} {
-		body, _ := json.Marshal(map[string]interface{}{"coffee_id": coffeeID, "quantity": 1})
+		body, _ := json.Marshal(map[string]any{"coffee_id": coffeeID, "quantity": 1})
 		req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 		w := httptest.NewRecorder()
 		handler.SetItem(w, req)
@@ -306,11 +311,11 @@ func TestClearCart(t *testing.T) {
 		Success bool `json:"success"`
 		Data    struct {
 			Cart struct {
-				Items []interface{} `json:"items"`
+				Items []any `json:"items"`
 			} `json:"cart"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if len(resp.Data.Cart.Items) != 0 {
 		t.Errorf("Expected 0 items after clear, got %d", len(resp.Data.Cart.Items))
@@ -319,7 +324,7 @@ func TestClearCart(t *testing.T) {
 
 func TestSetAddress(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -334,9 +339,9 @@ func TestSetAddress(t *testing.T) {
 	}
 	db.Create(&addr)
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
-	body, _ := json.Marshal(map[string]interface{}{"address_id": addr.ID})
+	body, _ := json.Marshal(map[string]any{"address_id": addr.ID})
 	req := authRequest("PUT", "/api/v1/cart/address", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetAddress(w, req)
@@ -358,7 +363,7 @@ func TestSetAddress(t *testing.T) {
 			} `json:"cart"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if resp.Data.Cart.AddressID == nil || *resp.Data.Cart.AddressID != addr.ID {
 		t.Errorf("Expected address_id %d, got %v", addr.ID, resp.Data.Cart.AddressID)
@@ -367,7 +372,7 @@ func TestSetAddress(t *testing.T) {
 
 func TestSetAddressWrongUser(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -388,9 +393,9 @@ func TestSetAddressWrongUser(t *testing.T) {
 	}
 	db.Create(&addr)
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
-	body, _ := json.Marshal(map[string]interface{}{"address_id": addr.ID})
+	body, _ := json.Marshal(map[string]any{"address_id": addr.ID})
 	req := authRequest("PUT", "/api/v1/cart/address", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetAddress(w, req)
@@ -402,7 +407,7 @@ func TestSetAddressWrongUser(t *testing.T) {
 
 func TestSetCard(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -416,9 +421,9 @@ func TestSetCard(t *testing.T) {
 	}
 	db.Create(&card)
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
-	body, _ := json.Marshal(map[string]interface{}{"card_id": card.ID})
+	body, _ := json.Marshal(map[string]any{"card_id": card.ID})
 	req := authRequest("PUT", "/api/v1/cart/card", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetCard(w, req)
@@ -440,7 +445,7 @@ func TestSetCard(t *testing.T) {
 			} `json:"cart"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if resp.Data.Cart.CardID == nil || *resp.Data.Cart.CardID != card.ID {
 		t.Errorf("Expected card_id %d, got %v", card.ID, resp.Data.Cart.CardID)
@@ -449,7 +454,7 @@ func TestSetCard(t *testing.T) {
 
 func TestSetCardWrongUser(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -468,9 +473,9 @@ func TestSetCardWrongUser(t *testing.T) {
 	}
 	db.Create(&card)
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
-	body, _ := json.Marshal(map[string]interface{}{"card_id": card.ID})
+	body, _ := json.Marshal(map[string]any{"card_id": card.ID})
 	req := authRequest("PUT", "/api/v1/cart/card", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetCard(w, req)
@@ -482,13 +487,13 @@ func TestSetCardWrongUser(t *testing.T) {
 
 func TestConvertCartMissingAddress(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	// Add item but no address or card
-	body, _ := json.Marshal(map[string]interface{}{"coffee_id": 1, "quantity": 1})
+	body, _ := json.Marshal(map[string]any{"coffee_id": 1, "quantity": 1})
 	req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetItem(w, req)
@@ -505,21 +510,21 @@ func TestConvertCartMissingAddress(t *testing.T) {
 
 func TestConvertCartMissingCard(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 	db := database.GetDB()
 
 	// Add item and address
-	body, _ := json.Marshal(map[string]interface{}{"coffee_id": 1, "quantity": 1})
+	body, _ := json.Marshal(map[string]any{"coffee_id": 1, "quantity": 1})
 	req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 	w := httptest.NewRecorder()
 	handler.SetItem(w, req)
 
 	addr := models.Address{UserID: user.ID, Name: "Test", Street: "123 St", City: "PDX", State: "OR", Zip: "97201", Country: "US"}
 	db.Create(&addr)
-	body, _ = json.Marshal(map[string]interface{}{"address_id": addr.ID})
+	body, _ = json.Marshal(map[string]any{"address_id": addr.ID})
 	req = authRequest("PUT", "/api/v1/cart/address", body, user.ID)
 	w = httptest.NewRecorder()
 	handler.SetAddress(w, req)
@@ -536,10 +541,10 @@ func TestConvertCartMissingCard(t *testing.T) {
 
 func TestConvertCartEmpty(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	// Empty cart convert
 	req := authRequest("POST", "/api/v1/cart/convert", nil, user.ID)
@@ -553,14 +558,14 @@ func TestConvertCartEmpty(t *testing.T) {
 
 func TestMultipleItems(t *testing.T) {
 	testDB, user := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 
 	// Add three different items
 	for i := uint(1); i <= 3; i++ {
-		body, _ := json.Marshal(map[string]interface{}{"coffee_id": i, "quantity": int(i)})
+		body, _ := json.Marshal(map[string]any{"coffee_id": i, "quantity": int(i)})
 		req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
 		w := httptest.NewRecorder()
 		handler.SetItem(w, req)
@@ -578,12 +583,12 @@ func TestMultipleItems(t *testing.T) {
 		Success bool `json:"success"`
 		Data    struct {
 			Cart struct {
-				Items    []interface{} `json:"items"`
-				Subtotal int           `json:"subtotal"`
+				Items    []any `json:"items"`
+				Subtotal int   `json:"subtotal"`
 			} `json:"cart"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if len(resp.Data.Cart.Items) != 3 {
 		t.Errorf("Expected 3 items, got %d", len(resp.Data.Cart.Items))
@@ -595,7 +600,7 @@ func TestMultipleItems(t *testing.T) {
 
 func TestCartIsolation(t *testing.T) {
 	testDB, user1 := setupCartTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -605,19 +610,19 @@ func TestCartIsolation(t *testing.T) {
 	}
 	db.Create(&user2)
 
-	handler := NewCartHandler("")
+	handler := NewCartHandler("", 0)
 	r := chi.NewRouter()
 	r.Put("/cart/item", handler.SetItem)
 	r.Get("/cart", handler.GetCart)
 
 	// User 1 adds item
-	body, _ := json.Marshal(map[string]interface{}{"coffee_id": 1, "quantity": 5})
+	body, _ := json.Marshal(map[string]any{"coffee_id": 1, "quantity": 5})
 	req := authRequest("PUT", "/cart/item", body, user1.ID)
 	w := httptest.NewRecorder()
 	r.ServeHTTP(w, req)
 
 	// User 2 adds different item
-	body, _ = json.Marshal(map[string]interface{}{"coffee_id": 2, "quantity": 3})
+	body, _ = json.Marshal(map[string]any{"coffee_id": 2, "quantity": 3})
 	req = authRequest("PUT", "/cart/item", body, user2.ID)
 	w = httptest.NewRecorder()
 	r.ServeHTTP(w, req)
@@ -638,7 +643,7 @@ func TestCartIsolation(t *testing.T) {
 			} `json:"cart"`
 		} `json:"data"`
 	}
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if len(resp.Data.Cart.Items) != 1 {
 		t.Fatalf("User 1 expected 1 item, got %d", len(resp.Data.Cart.Items))
@@ -655,7 +660,7 @@ func TestCartIsolation(t *testing.T) {
 	w = httptest.NewRecorder()
 	r.ServeHTTP(w, req)
 
-	json.NewDecoder(w.Body).Decode(&resp)
+	_ = json.NewDecoder(w.Body).Decode(&resp)
 
 	if len(resp.Data.Cart.Items) != 1 {
 		t.Fatalf("User 2 expected 1 item, got %d", len(resp.Data.Cart.Items))
@@ -664,3 +669,533 @@ func TestCartIsolation(t *testing.T) {
 		t.Errorf("User 2 expected coffee_id 2, got %d", resp.Data.Cart.Items[0].CoffeeID)
 	}
 }
+
+func TestConvertCartLimit(t *testing.T) {
+	cases := []struct {
+		name          string
+		capCents      int
+		quantity      int
+		expectOverCap bool
+	}{
+		{"over cap rejects", 20000, 41, true},   // $205
+		{"at cap accepts", 20000, 40, false},    // $200 boundary
+		{"under cap accepts", 20000, 39, false}, // $195
+		{"zero cap disables", 0, 1000, false},   // explicit off-switch
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			testDB, user := setupCartTestDB(t)
+			defer func() { _ = os.Remove(testDB) }()
+			defer database.ResetForTesting()
+
+			db := database.GetDB()
+			user.StripeCustomerID = "cus_test_overlimit"
+			if err := db.Save(&user).Error; err != nil {
+				t.Fatalf("saved user: %v", err)
+			}
+
+			addr := models.Address{
+				UserID: user.ID, Name: "Test", Street: "1 Main St",
+				City: "PDX", State: "OR", Zip: "97201", Country: "US",
+			}
+			if err := db.Create(&addr).Error; err != nil {
+				t.Fatalf("seed address: %v", err)
+			}
+
+			card := models.Card{
+				UserID: user.ID, StripePaymentID: "pm_test_overlimit",
+				Last4: "4242", Brand: "Visa", ExpMonth: 12, ExpYear: 2030,
+			}
+			if err := db.Create(&card).Error; err != nil {
+				t.Fatalf("seed card: %v", err)
+			}
+
+			// Pin coffee_id=4's price so cart-cap math stays stable across
+			// seed-price changes. The cap test is about (price * quantity)
+			// vs cap, not which coffee or what the menu currently charges.
+			const pinnedPrice = 500
+			if err := db.Model(&models.Coffee{}).Where("id = ?", 4).Update("price", pinnedPrice).Error; err != nil {
+				t.Fatalf("pin coffee price: %v", err)
+			}
+
+			handler := NewCartHandler("", tc.capCents)
+
+			body, _ := json.Marshal(map[string]any{"coffee_id": 4, "quantity": tc.quantity})
+			req := authRequest("PUT", "/api/v1/cart/item", body, user.ID)
+			w := httptest.NewRecorder()
+			handler.SetItem(w, req)
+			if w.Code != http.StatusOK {
+				t.Fatalf("SetItem: %d %s", w.Code, w.Body.String())
+			}
+
+			// set address
+			body, _ = json.Marshal(map[string]any{"address_id": addr.ID})
+			req = authRequest("PUT", "/api/v1/cart/address", body, user.ID)
+			w = httptest.NewRecorder()
+			handler.SetAddress(w, req)
+			if w.Code != http.StatusOK {
+				t.Fatalf("SetAddress: %d %s", w.Code, w.Body.String())
+			}
+
+			// set card
+			body, _ = json.Marshal(map[string]any{"card_id": card.ID})
+			req = authRequest("PUT", "/api/v1/cart/card", body, user.ID)
+			w = httptest.NewRecorder()
+			handler.SetCard(w, req)
+			if w.Code != http.StatusOK {
+				t.Fatalf("SetCard: %d %s", w.Code, w.Body.String())
+			}
+
+			// Capture audit slog ONLY for ConvertCart's emit window. Placed
+			// here (not at top of t.Run) so setup INFO logs from
+			// database.Connect/Migrate/Seed don't pollute the buffer with
+			// non-audit records - json.Unmarshal below requires a single
+			// JSON object, not multi-document input. slog.Default is
+			// process-global - do NOT add t.Parallel() to subtests here.
+			var auditBuf bytes.Buffer
+			if tc.expectOverCap {
+				prev := slog.Default()
+				slog.SetDefault(slog.New(slog.NewJSONHandler(&auditBuf, nil)))
+				t.Cleanup(func() { slog.SetDefault(prev) })
+			}
+
+			// Convert
+			req = authRequest("POST", "/api/v1/cart/convert", nil, user.ID)
+			w = httptest.NewRecorder()
+			handler.ConvertCart(w, req)
+
+			var resp struct {
+				Success bool `json:"success"`
+				Error   struct {
+					Code    string         `json:"code"`
+					Message string         `json:"message"`
+					Details map[string]any `json:"details"`
+				} `json:"error"`
+			}
+			_ = json.NewDecoder(w.Body).Decode(&resp)
+
+			isOverCap := w.Code == http.StatusBadRequest && resp.Error.Code == "CART_OVER_LIMIT"
+			if isOverCap != tc.expectOverCap {
+				t.Fatalf("expectOverCap=%v got code=%d errCode=%q msg=%q", tc.expectOverCap, w.Code, resp.Error.Code, resp.Error.Message)
+			}
+			if tc.expectOverCap {
+				if got, _ := resp.Error.Details["limit_cents"].(float64); int(got) != tc.capCents {
+					t.Errorf("limit_cents in details: want %d, got %v", tc.capCents, resp.Error.Details["limit_cents"])
+				}
+				if got, _ := resp.Error.Details["total_cents"].(float64); int(got) != tc.quantity*pinnedPrice {
+					t.Errorf("total_cents in details: want %d, got %v", tc.quantity*pinnedPrice, resp.Error.Details["total_cents"])
+				}
+
+				if auditBuf.Len() == 0 {
+					t.Fatalf("audit: expected cart_rejected slog line, got nothing")
+				}
+
+				var rec map[string]any
+				if err := json.Unmarshal(auditBuf.Bytes(), &rec); err != nil {
+					t.Fatalf("audit: decode slog record: %v\nraw: %s", err, auditBuf.String())
+				}
+				if got := rec["event"]; got != "cart_rejected" {
+					t.Errorf("audit event: want cart_rejected, got %v", got)
+				}
+				if n, _ := rec["user_id"].(float64); uint(n) != user.ID {
+					t.Errorf("audit user_id: want %d, got %v", user.ID, rec["user_id"])
+				}
+				if n, _ := rec["total_cents"].(float64); int(n) != tc.quantity*pinnedPrice {
+					t.Errorf("audit total_cents: want %d, got %v", tc.quantity*pinnedPrice, rec["total_cents"])
+				}
+				if n, _ := rec["cap_cents"].(float64); int(n) != tc.capCents {
+					t.Errorf("audit cap_cents: want %d, got %v", tc.capCents, rec["cap_cents"])
+				}
+			}
+		})
+	}
+}
+
+// TestSetCard_ExpiredReturns410 verifies that selecting an already-expired
+// card on the cart returns 410 + CARD_STORAGE_EXPIRED and soft-deletes the
+// card. Exercises cart.go SetCard expired-card branch
+func TestSetCard_ExpiredReturns410(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	past := time.Now().Add(-1 * time.Hour)
+	card := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_expired", Last4: "1111",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &past,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+
+	handler := NewCartHandler("", 0)
+	body, _ := json.Marshal(map[string]any{"card_id": card.ID})
+	req := authRequest("PUT", "/api/v1/cart/card", body, user.ID)
+	w := httptest.NewRecorder()
+	handler.SetCard(w, req)
+
+	if w.Code != http.StatusGone {
+		t.Fatalf("want 410, got %d, body: %s", w.Code, w.Body.String())
+	}
+	var resp struct {
+		Error struct {
+			Code string `json:"code"`
+		} `json:"error"`
+	}
+	_ = json.NewDecoder(w.Body).Decode(&resp)
+	if resp.Error.Code != "CARD_STORAGE_EXPIRED" {
+		t.Fatalf("want CARD_STORAGE_EXPIRED, got %q", resp.Error.Code)
+	}
+
+	var soft models.Card
+	if err := db.Unscoped().First(&soft, card.ID).Error; err != nil {
+		t.Fatalf("reload card unscoped: %v", err)
+	}
+	if !soft.DeletedAt.Valid {
+		t.Fatalf("expired card was not soft-deleted")
+	}
+}
+
+// TestConvertCart_ExpiredReturns410 verifies that attempting checkout with an
+// expired saved card shor-circuits at the validation step with 410 +
+// CARD_STORAGE_EXPIRED before any stripe interaction
+func TestConvertCart_ExpiredReturns410(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+
+	body, _ := json.Marshal(map[string]any{"coffee_id": 1, "quantity": 1})
+	req := authRequest("PUT", "/api/v1/vart/item", body, user.ID)
+	w := httptest.NewRecorder()
+	NewCartHandler("", 0).SetItem(w, req)
+
+	addr := models.Address{
+		UserID: user.ID, Name: "Test", Street: "123 St",
+		City: "PDX", State: "OR", Zip: "97201", Country: "US",
+	}
+	db.Create(&addr)
+	body, _ = json.Marshal(map[string]any{"address_id": addr.ID})
+	req = authRequest("PUT", "/api/v1/cart/address", body, user.ID)
+	w = httptest.NewRecorder()
+	NewCartHandler("", 0).SetAddress(w, req)
+
+	past := time.Now().Add(-1 * time.Hour)
+	card := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_expired", Last4: "1111",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &past,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+	if err := db.Model(&models.Cart{}).Where("user_id = ?", user.ID).Update("card_id", card.ID).Error; err != nil {
+		t.Fatalf("attach card to card: %v", err)
+	}
+
+	req = authRequest("POST", "/api/v1/cart/convert", nil, user.ID)
+	w = httptest.NewRecorder()
+	NewCartHandler("", 0).ConvertCart(w, req)
+
+	if w.Code != http.StatusGone {
+		t.Fatalf("want 410, got %d, body: %s", w.Code, w.Body.String())
+	}
+
+	var resp struct {
+		Error struct {
+			Code string `json:"code"`
+		} `json:"error"`
+	}
+	_ = json.NewDecoder(w.Body).Decode(&resp)
+	if resp.Error.Code != "CARD_STORAGE_EXPIRED" {
+		t.Fatalf("want CARD_STORAGE_EXPIRED, got %q", resp.Error.Code)
+	}
+}
+
+// TestRetryAuth exercises the pre-Stripe validation branches of
+// CartHandler.RetryAuth. The happy paths (Confirm → requires_action /
+// succeeded) hit the live Stripe API and aren't covered here — see
+// sca-psd2-compliance.md "Test plan" for manual coverage with the
+// 4000 0027 6000 3184 test card. Caveat #14 in that doc still applies:
+// NewCartHandler takes 2 args (appURL, maxOrderCents) and the seeded user
+// must have a non-empty StripeCustomerID so the Convert/Retry paths stay
+// hermetic.
+func TestRetryAuth(t *testing.T) {
+	cases := []struct {
+		name        string
+		ownedByUser bool
+		seedStatus  models.OrderStatus
+		seedPayment string
+		seedEvents  int
+		wantStatus  int
+		wantErrCode string
+	}{
+		{
+			name:        "wrong user returns not found",
+			ownedByUser: false, seedStatus: models.OrderStatusFailed,
+			seedPayment: "pi_test_wrong_user", seedEvents: 1,
+			wantStatus: http.StatusNotFound, wantErrCode: "ORDER_NOT_FOUND",
+		},
+		{
+			name:        "missing payment intent rejects",
+			ownedByUser: true, seedStatus: models.OrderStatusPending,
+			seedPayment: "", seedEvents: 0,
+			wantStatus: http.StatusConflict, wantErrCode: "INVALID_STATE",
+		},
+		{
+			name:        "paid order is not retryable",
+			ownedByUser: true, seedStatus: models.OrderStatusPaid,
+			seedPayment: "pi_test_paid", seedEvents: 1,
+			wantStatus: http.StatusConflict, wantErrCode: "INVALID_STATE",
+		},
+		{
+			name:        "refunded order is not retryable",
+			ownedByUser: true, seedStatus: models.OrderStatusRefunded,
+			seedPayment: "pi_test_refunded", seedEvents: 1,
+			wantStatus: http.StatusConflict, wantErrCode: "INVALID_STATE",
+		},
+		{
+			name:        "requires_action honors retry cap",
+			ownedByUser: true, seedStatus: models.OrderStatusRequiresAction,
+			seedPayment: "pi_test_req_action_cap", seedEvents: maxAuthIssuances,
+			wantStatus: http.StatusTooManyRequests, wantErrCode: "RETRY_LIMIT",
+		},
+		{
+			name:        "retry cap reached returns 429",
+			ownedByUser: true, seedStatus: models.OrderStatusFailed,
+			seedPayment: "pi_test_capped", seedEvents: maxAuthIssuances,
+			wantStatus: http.StatusTooManyRequests, wantErrCode: "RETRY_LIMIT",
+		},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			testDB, user := setupCartTestDB(t)
+			defer func() { _ = os.Remove(testDB) }()
+			defer database.ResetForTesting()
+
+			db := database.GetDB()
+			user.StripeCustomerID = "cus_test_retry"
+			if err := db.Save(&user).Error; err != nil {
+				t.Fatalf("save user: %v", err)
+			}
+
+			ownerID := user.ID
+			if !tc.ownedByUser {
+				other := models.User{
+					SSHKeyFingerprint: "SHA256:retryother",
+					SSHPublicKey:      "ssh-ed25519 AAAA retryother",
+				}
+				if err := db.Create(&other).Error; err != nil {
+					t.Fatalf("seed other user: %v", err)
+				}
+				ownerID = other.ID
+			}
+
+			card := models.Card{
+				UserID: ownerID, StripePaymentID: "pm_test_retry",
+				Last4: "4242", Brand: "Visa", ExpMonth: 12, ExpYear: 2030,
+			}
+			if err := db.Create(&card).Error; err != nil {
+				t.Fatalf("seed card: %v", err)
+			}
+
+			order := models.Order{
+				UserID:          ownerID,
+				CardID:          card.ID,
+				StripePaymentID: tc.seedPayment,
+				Status:          tc.seedStatus,
+				Subtotal:        500, Total: 500,
+				ShippingName: "Test", ShippingStreet: "1 Main St",
+				ShippingCity: "PDX", ShippingState: "OR",
+				ShippingZip: "97201", ShippingCountry: "US",
+			}
+			if err := db.Create(&order).Error; err != nil {
+				t.Fatalf("seed order: %v", err)
+			}
+
+			for i := 0; i < tc.seedEvents; i++ {
+				evt := models.OrderEvent{
+					OrderID: order.ID,
+					Type:    audit.EventOrderRequiresAction,
+					Actor:   fmt.Sprintf("user:%d", ownerID),
+					Payload: `{}`,
+				}
+				if err := db.Create(&evt).Error; err != nil {
+					t.Fatalf("seed event: %v", err)
+				}
+			}
+
+			handler := NewCartHandler("http://localhost", 0)
+			req := orderRequest("POST",
+				fmt.Sprintf("/api/v1/orders/%d/retry-auth", order.ID), nil, user.ID, fmt.Sprintf("%d", order.ID))
+			w := httptest.NewRecorder()
+			handler.RetryAuth(w, req)
+
+			if w.Code != tc.wantStatus {
+				t.Fatalf("status: want %d, got %d body=%s", tc.wantStatus, w.Code, w.Body.String())
+			}
+
+			var resp struct {
+				Error struct {
+					Code string `json:"code"`
+				} `json:"error"`
+			}
+			_ = json.NewDecoder(w.Body).Decode(&resp)
+			if resp.Error.Code != tc.wantErrCode {
+				t.Fatalf("err code: want %q, got %q, body=%s", tc.wantErrCode, resp.Error.Code, w.Body.String())
+			}
+		})
+	}
+}
+
+func TestRetryAuth_OrderNotFound(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	handler := NewCartHandler("http://localhost", 0)
+	req := orderRequest("POST", "/api/v1/orders/9999/retry-auth", nil, user.ID, "9999")
+	w := httptest.NewRecorder()
+	handler.RetryAuth(w, req)
+
+	if w.Code != http.StatusNotFound {
+		t.Fatalf("want 404, got %d body=%s", w.Code, w.Body.String())
+	}
+}
+
+func TestRespondRequiresAction_SetStatusRequiresAction(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	card := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_test_req_action",
+		Last4: "4242", Brand: "Visa", ExpMonth: 12, ExpYear: 2030,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+
+	order := models.Order{
+		UserID: user.ID, CardID: card.ID,
+		Status:   models.OrderStatusPending,
+		Subtotal: 500, Total: 500,
+		ShippingName: "Test", ShippingStreet: "1 Main St",
+		ShippingCity: "PDX", ShippingState: "OR",
+		ShippingZip: "97201", ShippingCountry: "US",
+	}
+	if err := db.Create(&order).Error; err != nil {
+		t.Fatalf("seed order: %v", err)
+	}
+
+	pi := &stripe.PaymentIntent{
+		ID: "pi_test_action_set",
+		NextAction: &stripe.PaymentIntentNextAction{
+			RedirectToURL: &stripe.PaymentIntentNextActionRedirectToURL{
+				URL: "https://hooks.stripe.com/redirect/test/test_3ds",
+			},
+		},
+	}
+
+	handler := NewCartHandler("http://localhost", 0)
+	w := httptest.NewRecorder()
+	handler.respondRequiresAction(w, &order, card.StripePaymentID, pi)
+
+	if w.Code != http.StatusAccepted {
+		t.Fatalf("want 202, got %d body=%s", w.Code, w.Body.String())
+	}
+
+	var resp struct {
+		Data struct {
+			OrderID         uint   `json:"order_id"`
+			PaymentIntentID string `json:"payment_intent_id"`
+			Status          string `json:"status"`
+			RedirectURL     string `json:"redirect_url"`
+		} `json:"data"`
+	}
+	if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
+		t.Fatalf("decode response: %v", err)
+	}
+	if resp.Data.Status != "requires_action" {
+		t.Fatalf("response status: %q, got %q", "requires_action", resp.Data.Status)
+	}
+	if resp.Data.RedirectURL == "" {
+		t.Fatalf("expected redirect url, got empty")
+	}
+	if resp.Data.PaymentIntentID != pi.ID {
+		t.Fatalf("payment intent id: want %q, got %q", pi.ID, resp.Data.PaymentIntentID)
+	}
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("order.Status: want %q, got %q", models.OrderStatusRequiresAction, reloaded.Status)
+	}
+	if reloaded.StripePaymentID != pi.ID {
+		t.Fatalf("order.StripePaymentID: want %q, got %q", pi.ID, reloaded.StripePaymentID)
+	}
+}
+
+// TestRespondRequiresAction_OverridesFailedFromWebhookRace simulates the race
+// described in sca-psd2-compliance.md note #3 / caveat #4: the
+// payment_intent.payment_failed webhook arrives BEFORE respondRequiresAction
+// returns and flips the row to OrderStatusFailed. The helper must override
+// that back to OrderStatusRequiresAction so the in-flight 3DS state surfaces
+// correctly to the TUI.
+func TestRespondRequiresAction_OverridesFailedFromWebhookRace(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	card := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_test_race",
+		Last4: "4242", Brand: "Visa", ExpMonth: 12, ExpYear: 2030,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+
+	order := models.Order{
+		UserID: user.ID, CardID: card.ID,
+		Status:   models.OrderStatusFailed,
+		Subtotal: 500, Total: 500,
+		ShippingName: "Test", ShippingStreet: "1 Main St",
+		ShippingCity: "PDX", ShippingState: "OR",
+		ShippingZip: "97201", ShippingCountry: "US",
+	}
+	if err := db.Create(&order).Error; err != nil {
+		t.Fatalf("seed order: %v", err)
+	}
+
+	pi := &stripe.PaymentIntent{
+		ID: "pi_test_race",
+		NextAction: &stripe.PaymentIntentNextAction{
+			RedirectToURL: &stripe.PaymentIntentNextActionRedirectToURL{
+				URL: "https://hooks.stripe.com/redirect/test_race",
+			},
+		},
+	}
+
+	handler := NewCartHandler("http://localhost", 0)
+	w := httptest.NewRecorder()
+	handler.respondRequiresAction(w, &order, card.StripePaymentID, pi)
+
+	if w.Code != http.StatusAccepted {
+		t.Fatalf("want 202, got %d body=%s", w.Code, w.Body.String())
+	}
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("override failed: want %q, got %q", models.OrderStatusRequiresAction, reloaded.Status)
+	}
+}

api/handlers/doc.go

@@ -0,0 +1,3 @@
+// Package handlers is where the real work happens, one function per endpoint:
+// carts, orders, products, addresses, cards, webhooks, and the rest.
+package handlers

api/handlers/orders.go

@@ -1,44 +1,177 @@
 package handlers
 
 import (
+	"encoding/json"
+	"fmt"
+	"log/slog"
 	"net/http"
+	"os"
 	"strconv"
+	"strings"
+	"time"
 
-	"github.com/go-chi/chi/v5"
-	"github.com/stripe/stripe-go/v78"
-	"github.com/stripe/stripe-go/v78/refund"
+	"terminalShop/pkg/bring"
+	"terminalShop/pkg/notify"
+	"terminalShop/pkg/shipping"
+	"terminalShop/pkg/shippo"
 
 	"terminalShop/api/middleware"
 	"terminalShop/pkg/audit"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
 	"terminalShop/pkg/utils"
+
+	"github.com/go-chi/chi/v5"
+	"github.com/stripe/stripe-go/v78"
+	"github.com/stripe/stripe-go/v78/refund"
+	"gorm.io/gorm"
 )
 
 type OrderHandler struct {
-	stripeKey string
+	bringAPIUID         string
+	bringAPIKey         string
+	bringCustomerNumber string
 }
 
-func NewOrderHandler(stripeSecretKey string) *OrderHandler {
-	return &OrderHandler{stripeKey: stripeSecretKey}
+type refundRequestPayload struct {
+	Reason  string `json:"reason"`
+	Message string `json:"message"`
+}
+
+// refundRequestCooldown is the minimum interval between customer-initiated
+// refund requests for the same order. Prevents accidental double-clicks and
+// repeated submissions from spamming the operator's Slack channel.
+const refundRequestCooldown = 15 * time.Minute
+
+// NewOrderHandler creates an order handler. Stripe credentials are wired
+// once at startup via stripe.Key in api/main.go.
+func NewOrderHandler(bringAPIUID, bringAPIKey, bringCustomerNumber string) *OrderHandler {
+	return &OrderHandler{
+		bringAPIUID:         bringAPIUID,
+		bringAPIKey:         bringAPIKey,
+		bringCustomerNumber: bringCustomerNumber,
+	}
+}
+
+// CreateRefundRequest posts a customer refund request into the order's Slack
+// thread. It does not issue a Stripe refund.
+func (h *OrderHandler) CreateRefundRequest(w http.ResponseWriter, r *http.Request) {
+	db := database.GetDB().WithContext(r.Context())
+	userID := middleware.UserIDFromContext(r.Context())
+
+	idStr := chi.URLParam(r, "id")
+	id, err := strconv.ParseUint(idStr, 10, 32)
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_ID", "invalid order id", nil)
+		return
+	}
+
+	var req refundRequestPayload
+	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_JSON", "invalid request body", nil)
+		return
+	}
+
+	req.Reason = strings.TrimSpace(req.Reason)
+	req.Message = strings.TrimSpace(req.Message)
+
+	if !models.IsValidRefundReason(req.Reason) {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_REASON", "invalid refund reason", nil)
+		return
+	}
+	if req.Reason == models.RefundRequestReasonOther && req.Message == "" {
+		utils.RespondError(w, http.StatusBadRequest, "MESSAGE_REQUIRED", "message is required when reason is other", nil)
+		return
+	}
+
+	var order models.Order
+	if err := db.Preload("User").Where("id = ? AND user_id = ?", id, userID).First(&order).Error; err != nil {
+		utils.RespondError(w, http.StatusNotFound, "ORDER_NOT_FOUND", "order not found", nil)
+		return
+	}
+	if !order.CanRequestRefund() {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_STATE",
+			"only paid, shipped, or delivered orders can request refunds", nil)
+		return
+	}
+
+	if order.LastRefundRequestAt != nil {
+		elapsed := time.Since(*order.LastRefundRequestAt)
+		if elapsed < refundRequestCooldown {
+			retryAfter := int((refundRequestCooldown - elapsed).Seconds()) + 1
+			w.Header().Set("Retry-After", strconv.Itoa(retryAfter))
+			utils.RespondError(w, http.StatusTooManyRequests, "RATE_LIMITED",
+				fmt.Sprintf("another refund request was submitted recently; try again in %d min", retryAfter/60+1),
+				nil)
+			return
+		}
+	}
+
+	text := fmt.Sprintf(":money_with_wings: *Refund request* — %s\n*From:* %s <%s>\n*Total:* $%.2f",
+		req.Reason, order.User.Name, order.User.Email, order.TotalInDollars())
+	if req.Message != "" {
+		quoted := "> " + strings.ReplaceAll(req.Message, "\n", "\n> ")
+		text += "\n\n" + quoted
+	}
+
+	if err := notify.SlackPostToOrderThreadBroadcast(order.ID, text); err != nil {
+		utils.RespondError(w, http.StatusBadGateway, "SLACK_ERROR", "failed to send refund request", nil)
+		return
+	}
+
+	// Record the timestamp after a successful Slack post so a Slack outage
+	// doesn't consume the user's cooldown — they can retry immediately.
+	if err := db.Model(&order).Update("last_refund_request_at", time.Now()).Error; err != nil {
+		slog.Warn("refund request: failed to record timestamp", "order_id", order.ID, "error", err)
+	}
+
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
+		"status": "sent",
+	})
 }
 
 func (h *OrderHandler) GetOrders(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var orders []models.Order
-	db.Where("user_id = ?", userID).Preload("Items").Order("created_at desc").Find(&orders)
+	db.Where("user_id = ?", userID).
+		Preload("Items").
+		Preload("Events", func(tx *gorm.DB) *gorm.DB { return tx.Order("created_at ASC") }).
+		Order("created_at desc").Find(&orders)
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"orders": orders,
 	})
 }
 
+func (h *OrderHandler) GetOrderStatus(w http.ResponseWriter, r *http.Request) {
+	db := database.GetDB().WithContext(r.Context())
+	userID := middleware.UserIDFromContext(r.Context())
+
+	idStr := chi.URLParam(r, "id")
+	id, err := strconv.ParseUint(idStr, 10, 32)
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_ID", "invalid order id", nil)
+		return
+	}
+
+	var order models.Order
+	if err := db.Where("id = ? AND user_id = ?", id, userID).First(&order).Error; err != nil {
+		utils.RespondError(w, http.StatusNotFound, "ORDER_NOT_FOUND", "order not found", nil)
+		return
+	}
+
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
+		"id":     order.ID,
+		"status": string(order.Status),
+	})
+}
+
 // RefundOrder issues a full refund for an order via Stripe and marks it as
 // refunded. Only orders in paid or shipped status can be refunded.
 func (h *OrderHandler) RefundOrder(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	idStr := chi.URLParam(r, "id")
@@ -67,8 +200,6 @@ func (h *OrderHandler) RefundOrder(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	stripe.Key = h.stripeKey
-
 	rf, err := refund.New(&stripe.RefundParams{
 		PaymentIntent: stripe.String(order.StripePaymentID),
 	})
@@ -88,8 +219,186 @@ func (h *OrderHandler) RefundOrder(w http.ResponseWriter, r *http.Request) {
 
 	audit.OrderRefunded(userID, order.ID, order.Total, rf.ID)
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"refund_id": rf.ID,
 		"status":    "refunded",
 	})
 }
+
+// updateTrackingRequest is the JSON body accepted by UpdateTracking.
+// shipped_at defaults to now if not otherwise specified
+type updateTrackingRequest struct {
+	Carrier        string     `json:"carrier"`
+	TrackingNumber string     `json:"tracking_number"`
+	TrackingURL    string     `json:"tracking_url"`
+	ShippedAt      *time.Time `json:"shipped_at"`
+}
+
+// UpdateTracking sets carrier metadata on the order. Transitions paid orders
+// to shipped automatically. Admin only, gated by RequireAdmin in routes.go,
+// not RequireAuth, so no user JWT is needed.
+func (h *OrderHandler) UpdateTracking(w http.ResponseWriter, r *http.Request) {
+	db := database.GetDB().WithContext(r.Context())
+
+	idStr := chi.URLParam(r, "id")
+	id, err := strconv.ParseUint(idStr, 10, 32)
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_ID", "invalid order id", nil)
+		return
+	}
+
+	var req updateTrackingRequest
+	if err := json.NewDecoder(r.Body).Decode(&req); err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_BODY", "invalid request body", nil)
+		return
+	}
+	if req.Carrier == "" || req.TrackingNumber == "" {
+		utils.RespondError(w, http.StatusBadRequest, "MISSING_FIELDS", "carrier and or tracking_number fields are required", nil)
+		return
+	}
+
+	var order models.Order
+	if err := db.Where("id = ?", id).First(&order).Error; err != nil {
+		utils.RespondError(w, http.StatusNotFound, "ORDER_NOT_FOUND", "order not found", nil)
+		return
+	}
+
+	shippedAt := req.ShippedAt
+	if shippedAt == nil {
+		now := time.Now()
+		shippedAt = &now
+	}
+
+	updates := map[string]any{
+		"carrier":         req.Carrier,
+		"tracking_number": req.TrackingNumber,
+		"tracking_url":    req.TrackingURL,
+		"shipped_at":      shippedAt,
+	}
+	if order.Status == models.OrderStatusPaid {
+		updates["status"] = models.OrderStatusShipped
+	}
+	if err := db.Model(&order).Updates(updates).Error; err != nil {
+		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to record shipment", nil)
+		return
+	}
+
+	audit.OrderShipped(order.UserID, order.ID, req.Carrier, req.TrackingNumber)
+
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
+		"order_id":        order.ID,
+		"carrier":         req.Carrier,
+		"tracking_number": req.TrackingNumber,
+		"status":          order.Status,
+	})
+}
+
+// PurchaseLabel buys a shipping label from shippo for the order, writes
+// the carrier, tracking, and label fields onto the order, and changes the status
+// from paid to shipped
+func (h *OrderHandler) PurchaseLabel(w http.ResponseWriter, r *http.Request) {
+	db := database.GetDB().WithContext(r.Context())
+
+	idStr := chi.URLParam(r, "id")
+	id, err := strconv.ParseUint(idStr, 10, 32)
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_ID", "invalid order id", nil)
+		return
+	}
+
+	var order models.Order
+	if err := db.Preload("Items.Coffee").Preload("User").Where("id = ?", id).First(&order).Error; err != nil {
+		utils.RespondError(w, http.StatusNotFound, "ORDER_NOT_FOUND", "order not found", nil)
+		return
+	}
+
+	if order.TrackingNumber != "" {
+		utils.RespondError(w, http.StatusConflict, "ALREADY_LABELED", "order already has a tracking number", nil)
+		return
+	}
+
+	if order.Status != models.OrderStatusPaid {
+		utils.RespondError(w, http.StatusConflict, "INVALID_STATE", "only paid orders can be labeled", nil)
+		return
+	}
+
+	const ozToKg = 0.0283495
+	const defaultOunces = 12.0
+
+	totalKg := 0.0
+	bringItems := make([]bring.LineItem, 0, len(order.Items))
+	shippoItems := make([]shippo.LineItem, 0, len(order.Items))
+	for _, item := range order.Items {
+		oz := float64(item.Coffee.Ounces)
+		if oz <= 0 {
+			oz = defaultOunces
+		}
+		kg := oz * ozToKg
+		totalKg += float64(item.Quantity) * kg
+		bringItems = append(bringItems, bring.LineItem{Title: item.Name, Quantity: item.Quantity, WeightKg: kg})
+		shippoItems = append(shippoItems, shippo.LineItem{Title: item.Name, Quantity: item.Quantity, WeightKg: kg})
+	}
+
+	var result *shipping.LabelResult
+	switch order.ShippingCountry {
+	case "US":
+		to := shippo.Address{
+			Name: order.ShippingName, Street1: order.ShippingStreet, Street2: order.ShippingStreet2,
+			City: order.ShippingCity, State: order.ShippingState, Country: order.ShippingCountry,
+			Zip: order.ShippingZip, Phone: order.ShippingPhone,
+		}
+		client := shippo.NewClient(os.Getenv("SHIPPO_API_KEY"))
+		result, err = client.CreateLabel(r.Context(), to, order.User.Email, shippoItems)
+		if err != nil {
+			utils.RespondError(w, http.StatusBadGateway, "SHIPPO_ERROR", err.Error(), nil)
+			return
+		}
+	case "NO":
+		to := bring.BookingAddress{
+			Name: order.ShippingName, Street1: order.ShippingStreet, Street2: order.ShippingStreet2,
+			City: order.ShippingCity, Country: order.ShippingCountry, Zip: order.ShippingZip,
+			Phone: order.ShippingPhone,
+		}
+		testMode := os.Getenv("ENVIRONMENT") != "production"
+		client := bring.NewBookingClient(h.bringAPIUID, h.bringAPIKey, h.bringCustomerNumber, testMode)
+		result, err = client.CreateLabel(r.Context(), to, order.User.Email, bringItems)
+		if err != nil {
+			utils.RespondError(w, http.StatusBadGateway, "BRING_ERROR", err.Error(), nil)
+			return
+		}
+	default:
+		utils.RespondError(w, http.StatusBadRequest, "UNSUPPORTED_DESTINATION", "no label vendor configured for this country", nil)
+		return
+	}
+
+	now := time.Now()
+	updates := map[string]any{
+		"carrier":               result.Carrier,
+		"tracking_number":       result.TrackingNumber,
+		"tracking_url":          result.TrackingURL,
+		"shipped_at":            &now,
+		"status":                models.OrderStatusShipped,
+		"shippo_transaction_id": result.TransactionID,
+		"label_url":             result.LabelURL,
+		"label_cost_cents":      result.CostCents,
+	}
+	if err := db.Model(&order).Updates(updates).Error; err != nil {
+		audit.LabelOrphaned(order.ID, result.TransactionID, result.TrackingNumber, err)
+		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "label purchased but failed to record on order; ops will reconcile", nil)
+		return
+	}
+
+	audit.LabelPurchased(order.ID, result.Carrier, result.TrackingNumber, result.TransactionID, result.CostCents)
+	go notify.SlackUnpinOrder(order.ID)
+
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
+		"order_id":        order.ID,
+		"carrier":         result.Carrier,
+		"service":         result.ServiceLevel,
+		"tracking_number": result.TrackingNumber,
+		"tracking_url":    result.TrackingURL,
+		"label_url":       result.LabelURL,
+		"cost_cents":      result.CostCents,
+		"status":          models.OrderStatusShipped,
+	})
+}

api/handlers/orders_test.go

@@ -0,0 +1,170 @@
+package handlers
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"net/http"
+	"net/http/httptest"
+	"path/filepath"
+	"testing"
+	"time"
+
+	"github.com/go-chi/chi/v5"
+
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+)
+
+func setupOrderTestDB(t *testing.T) models.User {
+	t.Helper()
+	testDB := filepath.Join(t.TempDir(), "orders.db")
+	database.ResetForTesting()
+	t.Cleanup(database.ResetForTesting)
+
+	db, err := database.Connect(testDB)
+	if err != nil {
+		t.Fatalf("failed to connect to test database: %v", err)
+	}
+	if err := database.Migrate(db); err != nil {
+		t.Fatalf("failed to migrate: %v", err)
+	}
+	if err := database.Seed(db); err != nil {
+		t.Fatalf("failed to seed: %v", err)
+	}
+
+	user := models.User{
+		SSHKeyFingerprint: "SHA256:ordertestfingerprint",
+		SSHPublicKey:      "ssh-ed25519 AAAA ordertestkey",
+		Name:              "Order Test User",
+		Email:             "orders@example.com",
+	}
+	if err := db.Create(&user).Error; err != nil {
+		t.Fatalf("failed to create test user: %v", err)
+	}
+
+	return user
+}
+
+func orderRequest(method, url string, body []byte, userID uint, orderID string) *http.Request {
+	req := authRequest(method, url, body, userID)
+	routeCtx := chi.NewRouteContext()
+	routeCtx.URLParams.Add("id", orderID)
+	return req.WithContext(contextWithRoute(req.Context(), routeCtx))
+}
+
+func contextWithRoute(ctx context.Context, routeCtx *chi.Context) context.Context {
+	return context.WithValue(ctx, chi.RouteCtxKey, routeCtx)
+}
+
+func TestCreateRefundRequestRequiresMessageForOther(t *testing.T) {
+	user := setupOrderTestDB(t)
+
+	handler := NewOrderHandler("", "", "")
+	body := []byte(`{"reason":"Other","message":"   "}`)
+	req := orderRequest("POST", "/api/v1/orders/1/refund-request", body, user.ID, "1")
+	w := httptest.NewRecorder()
+
+	handler.CreateRefundRequest(w, req)
+
+	if w.Code != http.StatusBadRequest {
+		t.Fatalf("expected status 400, got %d", w.Code)
+	}
+
+	var resp struct {
+		Error struct {
+			Code string `json:"code"`
+		} `json:"error"`
+	}
+	if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
+		t.Fatalf("failed to decode response: %v", err)
+	}
+	if resp.Error.Code != "MESSAGE_REQUIRED" {
+		t.Errorf("expected MESSAGE_REQUIRED, got %q", resp.Error.Code)
+	}
+}
+
+func TestCreateRefundRequestRejectsInvalidOrderState(t *testing.T) {
+	user := setupOrderTestDB(t)
+
+	db := database.GetDB()
+	order := models.Order{
+		UserID:       user.ID,
+		CardID:       1,
+		Status:       models.OrderStatusFailed,
+		Subtotal:     100,
+		ShippingCost: 0,
+		Total:        100,
+	}
+	if err := db.Create(&order).Error; err != nil {
+		t.Fatalf("failed to create order: %v", err)
+	}
+
+	handler := NewOrderHandler("", "", "")
+	body := []byte(`{"reason":"Quality issue","message":""}`)
+	req := orderRequest("POST", "/api/v1/orders/1/refund-request", body, user.ID, fmt.Sprintf("%d", order.ID))
+	w := httptest.NewRecorder()
+
+	handler.CreateRefundRequest(w, req)
+
+	if w.Code != http.StatusBadRequest {
+		t.Fatalf("expected status 400, got %d", w.Code)
+	}
+
+	var resp struct {
+		Error struct {
+			Code string `json:"code"`
+		} `json:"error"`
+	}
+	if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
+		t.Fatalf("failed to decode response: %v", err)
+	}
+	if resp.Error.Code != "INVALID_STATE" {
+		t.Errorf("expected INVALID_STATE, got %q", resp.Error.Code)
+	}
+}
+
+func TestCreateRefundRequestEnforcesCooldown(t *testing.T) {
+	user := setupOrderTestDB(t)
+
+	db := database.GetDB()
+	recent := time.Now().Add(-1 * time.Minute)
+	order := models.Order{
+		UserID:              user.ID,
+		CardID:              1,
+		Status:              models.OrderStatusPaid,
+		Subtotal:            100,
+		ShippingCost:        0,
+		Total:               100,
+		LastRefundRequestAt: &recent,
+	}
+	if err := db.Create(&order).Error; err != nil {
+		t.Fatalf("failed to create order: %v", err)
+	}
+
+	handler := NewOrderHandler("", "", "")
+	body := []byte(`{"reason":"Quality issue","message":""}`)
+	req := orderRequest("POST", "/api/v1/orders/1/refund-request", body, user.ID, fmt.Sprintf("%d", order.ID))
+	w := httptest.NewRecorder()
+
+	handler.CreateRefundRequest(w, req)
+
+	if w.Code != http.StatusTooManyRequests {
+		t.Fatalf("expected status 429, got %d", w.Code)
+	}
+	if got := w.Header().Get("Retry-After"); got == "" {
+		t.Errorf("expected Retry-After header, got empty")
+	}
+
+	var resp struct {
+		Error struct {
+			Code string `json:"code"`
+		} `json:"error"`
+	}
+	if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
+		t.Fatalf("failed to decode response: %v", err)
+	}
+	if resp.Error.Code != "RATE_LIMITED" {
+		t.Errorf("expected RATE_LIMITED, got %q", resp.Error.Code)
+	}
+}

api/handlers/products.go

@@ -20,7 +20,7 @@ func NewProductHandler() *ProductHandler {
 
 // GetProducts returns all products from the database
 func (h *ProductHandler) GetProducts(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 
 	var products []models.Coffee
 
@@ -30,14 +30,14 @@ func (h *ProductHandler) GetProducts(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"products": products,
 	})
 }
 
 // GetProduct returns a single product by ID
 func (h *ProductHandler) GetProduct(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 
 	// Get ID from URL parameter
 	idStr := chi.URLParam(r, "id")
@@ -53,7 +53,7 @@ func (h *ProductHandler) GetProduct(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"product": product,
 	})
 }

api/handlers/products_test.go

@@ -16,7 +16,7 @@ func setupTestDB(t *testing.T) string {
 	testDB := "test_products.db"
 
 	// Remove if exists
-	os.Remove(testDB)
+	_ = os.Remove(testDB)
 
 	// Reset singleton
 	database.ResetForTesting()
@@ -39,7 +39,7 @@ func setupTestDB(t *testing.T) string {
 
 func TestGetProduct(t *testing.T) {
 	testDB := setupTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	handler := NewProductHandler()
@@ -78,7 +78,7 @@ func TestGetProduct(t *testing.T) {
 
 func TestGetProductNotFound(t *testing.T) {
 	testDB := setupTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	handler := NewProductHandler()
@@ -98,7 +98,7 @@ func TestGetProductNotFound(t *testing.T) {
 
 func TestGetProductsEmptyDatabase(t *testing.T) {
 	testDB := "test_empty.db"
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	// Create database but don't seed

api/handlers/reconcile.go

@@ -1,25 +1,35 @@
 package handlers
 
 import (
+	"context"
 	"fmt"
-	"log"
+	"log/slog"
 	"time"
 
+	"terminalShop/api/middleware"
+	"terminalShop/pkg/audit"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
+	"terminalShop/pkg/notify"
 
 	"github.com/stripe/stripe-go/v78"
 	"github.com/stripe/stripe-go/v78/paymentintent"
 	"gorm.io/gorm"
 )
 
+// paymentIntentGetFn lets tests stub the Stripe Get call without spinning
+// up an httptest backend. Production callers go straight through to the
+// real paymentintent.Get.
+var paymentIntentGetFn = paymentintent.Get
+
+func reconcileLog() *slog.Logger { return slog.With("component", "reconcile") }
+
 // ReconcileOrders finds pending orders with no Stripe ID older than 10 minutes
 // and checks whether Stripe has a succeeded PaymentIntent for them. This fixes
 // the case where the server crashed after charging but before the DB transaction
 // completed.
-func ReconcileOrders(stripeKey string) {
-	stripe.Key = stripeKey
-	db := database.GetDB()
+func ReconcileOrders(ctx context.Context) {
+	db := database.GetDB().WithContext(ctx)
 
 	var orders []models.Order
 	cutoff := time.Now().Add(-10 * time.Minute)
@@ -30,22 +40,28 @@ func ReconcileOrders(stripeKey string) {
 		return
 	}
 
-	log.Printf("[reconcile] checking %d pending orders", len(orders))
+	reconcileLog().Info("checking pending orders", "count", len(orders))
 
 	for _, order := range orders {
+		if err := ctx.Err(); err != nil {
+			reconcileLog().Info("reconcile orders cancelled mid-loop", "error", err)
+			return
+		}
 		params := &stripe.PaymentIntentSearchParams{
 			SearchParams: stripe.SearchParams{
-				Query: fmt.Sprintf("metadata['order_id']:'%d' AND status:'succeeded'", order.ID),
+				Context: ctx,
+				Query:   fmt.Sprintf("metadata['order_id']:'%d' AND status:'succeeded'", order.ID),
 			},
 		}
 
 		iter := paymentintent.Search(params)
 		for iter.Next() {
 			pi := iter.PaymentIntent()
-			log.Printf("[reconcile] found succeeded PI %s for order %d — patching", pi.ID, order.ID)
+			reconcileLog().Warn("found succeeded payment intent for unrecorded order — patching",
+				"order_id", order.ID, "pi", pi.ID)
 
 			txErr := db.Transaction(func(tx *gorm.DB) error {
-				if err := tx.Model(&order).Updates(map[string]interface{}{
+				if err := tx.Model(&order).Updates(map[string]any{
 					"status":            models.OrderStatusPaid,
 					"stripe_payment_id": pi.ID,
 				}).Error; err != nil {
@@ -58,17 +74,193 @@ func ReconcileOrders(stripeKey string) {
 				if err := tx.Where("cart_id = ?", cart.ID).Delete(&models.CartItem{}).Error; err != nil {
 					return err
 				}
-				return tx.Model(&cart).Updates(map[string]interface{}{
+				return tx.Model(&cart).Updates(map[string]any{
 					"address_id": nil,
 					"card_id":    nil,
 				}).Error
 			})
 			if txErr != nil {
-				log.Printf("[reconcile] failed to patch order %d: %v", order.ID, txErr)
+				reconcileLog().Error("failed to patch order", "order_id", order.ID, "error", txErr)
 			}
 		}
 		if err := iter.Err(); err != nil {
-			log.Printf("[reconcile] stripe search error for order %d: %v", order.ID, err)
+			reconcileLog().Error("stripe search error", "order_id", order.ID, "error", err)
 		}
 	}
 }
+
+// ReconcileStale3DSOrders flips requires_action orders that have been
+// awaiting the customer's 3DS challenge longer than threshold to failed,
+// after re-checking the PaymentIntent with Stripe so a late
+// payment_intent.succeeded webhook is respected. Deliberately separate
+// from ReconcileOrders: the empty-PI predicate there is load-bearing for
+// the crash-mid-create case (see sca-psd2-compliance.md caveat #20).
+// stripe.Key is wired once at startup in api/main.go.
+func ReconcileStale3DSOrders(ctx context.Context, threshold time.Duration) {
+	db := database.GetDB().WithContext(ctx)
+
+	var orders []models.Order
+	// Predicate keys off updated_at, not created_at: respondRequiresAction
+	// and RetryAuth both bump updated_at via GORM auto-stamping, so every
+	// customer-driven retry extends the grace window. Intentional - sweeping
+	// a row the customer just re-armed would race the new challenge.
+	cutoff := time.Now().Add(-threshold)
+	if err := db.Where("status = ? AND updated_at < ?",
+		models.OrderStatusRequiresAction, cutoff).Find(&orders).Error; err != nil {
+		reconcileLog().Error("stale 3ds scan failed", "error", err)
+		return
+	}
+	if len(orders) == 0 {
+		return
+	}
+
+	reconcileLog().Info("checking stale requires_action orders", "count", len(orders))
+
+	piParams := &stripe.PaymentIntentParams{Params: stripe.Params{Context: ctx}}
+	for i := range orders {
+		if err := ctx.Err(); err != nil {
+			reconcileLog().Info("stale 3ds sweep cancelled mid-loop", "error", err)
+			return
+		}
+		order := &orders[i]
+		if order.StripePaymentID == "" {
+			// respondRequiresAction writes stripe_payment_id and status in
+			// one UPDATE so this should be unreachable; guard anyway so a
+			// future regression noisily logs instead of 4xx'ing Stripe.
+			reconcileLog().Warn("requires_action row missing PI id; skipping", "order_id", order.ID)
+			middleware.RecordAbandoned3DSSweep("missing_pi")
+			continue
+		}
+		actual, err := paymentIntentGetFn(order.StripePaymentID, piParams)
+		if err != nil {
+			reconcileLog().Error("stripe get failed",
+				"order_id", order.ID, "pi", order.StripePaymentID, "error", err)
+			middleware.RecordAbandoned3DSSweep("stripe_error")
+			continue
+		}
+		switch actual.Status {
+		case stripe.PaymentIntentStatusSucceeded:
+			// Stripe says paid but our row still says requires_action, the
+			// payment_intent.succeeded webhook has not landed yet (or was
+			//  dropped). Defer to handlePaymentIntentsucceeded; it owns the
+			// paid transition + cart cleanup atomically. The next sweep
+			// tick re-checks and surfaces the dropped webhook if it persists
+			reconcileLog().Warn("stripe reports succeeded for requires_action row; deferring to webhook",
+				"order_id", order.ID, "pi", order.StripePaymentID)
+			middleware.RecordAbandoned3DSSweep("succeeded_skip")
+		case stripe.PaymentIntentStatusProcessing,
+			stripe.PaymentIntentStatusRequiresCapture:
+			reconcileLog().Info("payment intent still transitioning; skipping",
+				"order_id", order.ID, "pi", order.StripePaymentID, "stripe_status", string(actual.Status))
+			middleware.RecordAbandoned3DSSweep("processing_skip")
+		case stripe.PaymentIntentStatusRequiresAction,
+			stripe.PaymentIntentStatusRequiresPaymentMethod,
+			stripe.PaymentIntentStatusRequiresConfirmation,
+			stripe.PaymentIntentStatusCanceled:
+			flipStale3DSToFailed(db, order, string(actual.Status))
+		default:
+			reconcileLog().Warn("unrecognized stripe status; skipping",
+				"order_id", order.ID, "pi", order.StripePaymentID, "stripe_status", string(actual.Status))
+			middleware.RecordAbandoned3DSSweep("unrecognized_status")
+		}
+	}
+}
+
+// flipStale3DSToFailed transitions a single stale requires_action row
+// to failed. The UPDATE is conditional on status = requires_action so a
+// payment_intent.succeeded webhook that landed between the stripe get and
+// this write (caveat #20 race) wins and we silently no-op
+func flipStale3DSToFailed(db *gorm.DB, order *models.Order, stripeStatus string) {
+	// Map form so the single-field UPDATE is explicit at the call site.
+	// GORM still auto-stamps updated_at; the row exits the sweep predicate
+	// naturally on the next tick because status no longer matches anyway.
+	res := db.Model(&models.Order{}).
+		Where("id = ? AND status = ?", order.ID, models.OrderStatusRequiresAction).
+		Updates(map[string]any{"status": models.OrderStatusFailed})
+	if res.Error != nil {
+		reconcileLog().Error("flip stale 3ds failed", "order_id", order.ID, "error", res.Error)
+		middleware.RecordAbandoned3DSSweep("flip_failed")
+		return
+	}
+	if res.RowsAffected == 0 {
+		reconcileLog().Info("stale 3ds row already transitioned; sweep no-op",
+			"order_id", order.ID)
+		middleware.RecordAbandoned3DSSweep("flip_noop")
+		return
+	}
+	audit.Order3DSAbandoned(order.UserID, order.ID, order.StripePaymentID)
+	reconcileLog().Info("3ds abandoned order flipped to failed",
+		"order_id", order.ID, "pi", order.StripePaymentID, "stripe_status", stripeStatus)
+	middleware.RecordAbandoned3DSSweep("flipped")
+}
+
+// ReconcileExpiredCards removes saved cards whose retention deadline elapsed.
+// Read paths filter out expired rows so users never see them; this job drives
+// the Stripe detach + audit + physical row delete out of band so request
+// handlers never block on Stripe API calls during a card sweep.
+func ReconcileExpiredCards(ctx context.Context) {
+	db := database.GetDB().WithContext(ctx)
+
+	var cards []models.Card
+	if err := db.Where(
+		"storage_expires_at IS NOT NULL AND storage_expires_at <= ?",
+		time.Now(),
+	).Find(&cards).Error; err != nil {
+		reconcileLog().Error("expired card scan failed", "error", err)
+		return
+	}
+	if len(cards) == 0 {
+		return
+	}
+
+	reconcileLog().Info("expiring inactive saved cards", "count", len(cards))
+	for i := range cards {
+		if err := ctx.Err(); err != nil {
+			reconcileLog().Info("card sweep cancelled mid-loop", "error", err)
+			return
+		}
+		if err := expireStoredCard(db, &cards[i]); err != nil {
+			reconcileLog().Error("expire card failed", "card_id", cards[i].ID, "error", err)
+		}
+	}
+}
+
+// ReconcilePayRedirects deletes pay_redirects rows whose ExpiresAt had passed.
+// Lazy deletion on read (PayRedirect) is the primary path, this sweep only
+// reclaims tokens nobody ever followed so the table stays bounded.
+func ReconcilePayRedirects(ctx context.Context) {
+	db := database.GetDB().WithContext(ctx)
+
+	res := db.Where("expires_at < ?", time.Now()).Delete(&models.PayRedirect{})
+	if res.Error != nil {
+		reconcileLog().Error("pay_redirects sweep failed", "error", res.Error)
+		return
+	}
+	if res.RowsAffected == 0 {
+		return
+	}
+	reconcileLog().Info("swept expired pay_redirects", "count", res.RowsAffected)
+}
+
+// ReconcileUnshipped finds paid orders older than 24h with no tracking
+// number and posts a single Slack reminder. Pure read + notify.
+func ReconcileUnshipped(ctx context.Context) {
+	db := database.GetDB().WithContext(ctx)
+
+	var orders []models.Order
+	cutoff := time.Now().Add(-24 * time.Hour)
+	err := db.Where(
+		"status = ? AND (tracking_number = '' OR tracking_number IS NULL) AND created_at < ?",
+		models.OrderStatusPaid, cutoff,
+	).Order("created_at ASC").Find(&orders).Error
+	if err != nil {
+		reconcileLog().Error("unshipped query failed", "error", err)
+		return
+	}
+	if len(orders) == 0 {
+		return
+	}
+
+	reconcileLog().Info("unshipped orders found", "count", len(orders))
+	notify.SlackUnshippedReminder(orders)
+}

api/handlers/reconcile_test.go

@@ -0,0 +1,598 @@
+package handlers
+
+import (
+	"context"
+	"fmt"
+	"os"
+	"testing"
+	"time"
+
+	"terminalShop/api/middleware"
+	"terminalShop/pkg/audit"
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+
+	"github.com/prometheus/client_golang/prometheus/testutil"
+	"github.com/stripe/stripe-go/v78"
+)
+
+// TestReconcileStale3DSOrders_FlipsAbandonedToFailed verifies the predicate
+// and Stripe-Get branching: a row past the threshold whose PaymentIntent
+// Stripe still reports as requires_payment_method (the customer never
+// completed the challenge) transitions to failed and emits the new
+// order_3ds_abandoned audit row.
+func TestReconcileStale3DSOrders_FlipsAbandonedToFailed(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_stale_abandoned",
+		time.Now().Add(-1*time.Hour))
+
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatusRequiresPaymentMethod,
+		}, nil
+	}
+
+	flipped := middleware.Abandoned3DSSweepCounter().WithLabelValues("flipped")
+	before := testutil.ToFloat64(flipped)
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusFailed {
+		t.Fatalf("status: want %q, got %q", models.OrderStatusFailed, reloaded.Status)
+	}
+
+	var events []models.OrderEvent
+	if err := db.Where("order_id = ? AND type = ?",
+		order.ID, audit.EventOrder3DSAbandoned).Find(&events).Error; err != nil {
+		t.Fatalf("list events: %v", err)
+	}
+	if len(events) != 1 {
+		t.Fatalf("want 1 order_3ds_abandoned audit row, got %d", len(events))
+	}
+	if got := testutil.ToFloat64(flipped) - before; got != 1 {
+		t.Fatalf("want 1 flipped sweep counter increment, got %v", got)
+	}
+}
+
+// TestReconcileStale3DSOrders_SkipsRecent verifies the threshold predicate
+// excludes rows still within the grace window. A fresh requires_action row
+// must not even reach the Stripe Get call.
+func TestReconcileStale3DSOrders_SkipsRecent(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_fresh_3ds",
+		time.Now().Add(-5*time.Minute))
+
+	called := false
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		called = true
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatusRequiresPaymentMethod,
+		}, nil
+	}
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	if called {
+		t.Fatalf("stripe Get called for in-window row")
+	}
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("status changed unexpectedly: %q", reloaded.Status)
+	}
+}
+
+// TestReconcileStale3DSOrders_SkipsWhenStripeSaysSucceeded covers the
+// webhook-race guard from caveat #20. If Stripe-side already says succeeded,
+// the sweep must defer to handlePaymentIntentSucceeded rather than overwrite
+// the authoritative end state.
+func TestReconcileStale3DSOrders_SkipsWhenStripeSaysSucceeded(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_succeeded_late_webhook",
+		time.Now().Add(-1*time.Hour))
+
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatusSucceeded,
+		}, nil
+	}
+
+	skip := middleware.Abandoned3DSSweepCounter().WithLabelValues("succeeded_skip")
+	before := testutil.ToFloat64(skip)
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("must defer to webhook on succeeded; got %q", reloaded.Status)
+	}
+	if got := testutil.ToFloat64(skip) - before; got != 1 {
+		t.Fatalf("want 1 succeeded_skip sweep counter increment, got %v", got)
+	}
+}
+
+// TestReconcileStale3DSOrders_GuardsAgainstWebhookRace covers the conditional
+// UPDATE. If the row flipped to paid between the Stripe Get and the flip,
+// the WHERE status = requires_action clause prevents clobber.
+func TestReconcileStale3DSOrders_GuardsAgainstWebhookRace(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_race_paid",
+		time.Now().Add(-1*time.Hour))
+
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		db.Model(&models.Order{}).Where("id = ?", order.ID).
+			Update("status", models.OrderStatusPaid)
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatusRequiresPaymentMethod,
+		}, nil
+	}
+
+	noop := middleware.Abandoned3DSSweepCounter().WithLabelValues("flip_noop")
+	before := testutil.ToFloat64(noop)
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusPaid {
+		t.Fatalf("conditional update must preserve paid; got %q", reloaded.Status)
+	}
+	if got := testutil.ToFloat64(noop) - before; got != 1 {
+		t.Fatalf("want 1 flip_noop sweep counter increment, got %v", got)
+	}
+}
+
+// TestReconcileStale3DSOrders_FlipsCanceledPI covers the canceled-PI branch:
+// Stripe-terminal-canceled maps to OrderStatusFailed (matches RetryAuth's
+// existing precedent — see api/handlers/cart.go RetryAuth canceled branch).
+func TestReconcileStale3DSOrders_FlipsCanceledPI(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_canceled_stale",
+		time.Now().Add(-1*time.Hour))
+
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatusCanceled,
+		}, nil
+	}
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusFailed {
+		t.Fatalf("canceled PI must flip to failed; got %q", reloaded.Status)
+	}
+}
+
+// TestReconcileStale3DSOrders_DoesNotConsumeRetryCap regression-tests the
+// caveat #17 decoupling: the new sweep emits EventOrder3DSAbandoned, never
+// EventOrderRequiresAction, so a swept-then-stuck order does not silently
+// shrink the retry ceiling for any future user-driven retry attempts.
+func TestReconcileStale3DSOrders_DoesNotConsumeRetryCap(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_decoupled_cap",
+		time.Now().Add(-1*time.Hour))
+
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatusRequiresPaymentMethod,
+		}, nil
+	}
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	var retryCount int64
+	if err := db.Model(&models.OrderEvent{}).
+		Where("order_id = ? AND type = ?", order.ID, audit.EventOrderRequiresAction).
+		Count(&retryCount).Error; err != nil {
+		t.Fatalf("count retry events: %v", err)
+	}
+	if retryCount != 0 {
+		t.Fatalf("sweep must not emit EventOrderRequiresAction; got %d", retryCount)
+	}
+}
+
+// TestReconcileStale3DSOrders_SkipsTransitioningStatuses covers the
+// processing and requires_capture branches: Stripe still owns the PI's
+// next move, so the sweep must not flip even past the threshold.
+func TestReconcileStale3DSOrders_SkipsTransitioningStatuses(t *testing.T) {
+	cases := []struct {
+		name   string
+		status stripe.PaymentIntentStatus
+	}{
+		{"processing", stripe.PaymentIntentStatusProcessing},
+		{"requires_capture", stripe.PaymentIntentStatusRequiresCapture},
+	}
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			testDB, user := setupCartTestDB(t)
+			defer func() { _ = os.Remove(testDB) }()
+			defer database.ResetForTesting()
+
+			db := database.GetDB()
+			audit.SetDB(db)
+			defer audit.SetDB(nil)
+
+			order := seedRequiresActionOrder(t, user.ID,
+				"pi_transitioning_"+tc.name, time.Now().Add(-1*time.Hour))
+
+			orig := paymentIntentGetFn
+			defer func() { paymentIntentGetFn = orig }()
+			paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+				return &stripe.PaymentIntent{ID: id, Status: tc.status}, nil
+			}
+
+			skip := middleware.Abandoned3DSSweepCounter().WithLabelValues("processing_skip")
+			before := testutil.ToFloat64(skip)
+
+			ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+			var reloaded models.Order
+			if err := db.First(&reloaded, order.ID).Error; err != nil {
+				t.Fatalf("reload: %v", err)
+			}
+			if reloaded.Status != models.OrderStatusRequiresAction {
+				t.Fatalf("%s must stay requires_action; got %q", tc.name, reloaded.Status)
+			}
+			if got := testutil.ToFloat64(skip) - before; got != 1 {
+				t.Fatalf("want 1 processing_skip increment, got %v", got)
+			}
+		})
+	}
+}
+
+// TestReconcileStale3DSOrders_SkipsUnknownStatus covers the switch's default
+// arm: an unrecognized Stripe status logs and skips rather than guessing a
+// transition. Defends against new PI statuses appearing in future SDKs.
+func TestReconcileStale3DSOrders_SkipsUnknownStatus(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_unknown_status",
+		time.Now().Add(-1*time.Hour))
+
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatus("some_new_future_status"),
+		}, nil
+	}
+
+	unknown := middleware.Abandoned3DSSweepCounter().WithLabelValues("unrecognized_status")
+	before := testutil.ToFloat64(unknown)
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("unknown status must not flip; got %q", reloaded.Status)
+	}
+	if got := testutil.ToFloat64(unknown) - before; got != 1 {
+		t.Fatalf("want 1 unrecognized_status increment, got %v", got)
+	}
+}
+
+// TestReconcileStale3DSOrders_SkipsOnStripeError verifies a Stripe Get
+// failure logs and leaves the row alone. Transient network errors must not
+// look like an abandoned 3DS.
+func TestReconcileStale3DSOrders_SkipsOnStripeError(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_stripe_error",
+		time.Now().Add(-1*time.Hour))
+
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(_ string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		return nil, fmt.Errorf("simulated stripe outage")
+	}
+
+	stripeErr := middleware.Abandoned3DSSweepCounter().WithLabelValues("stripe_error")
+	before := testutil.ToFloat64(stripeErr)
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("stripe error must not flip; got %q", reloaded.Status)
+	}
+	if got := testutil.ToFloat64(stripeErr) - before; got != 1 {
+		t.Fatalf("want 1 stripe_error sweep counter increment, got %v", got)
+	}
+}
+
+// TestReconcileStale3DSOrders_SkipsEmptyPaymentIntentID guards the
+// defensive empty-PI short-circuit: even past the threshold, a row missing
+// stripe_payment_id must not reach paymentintent.Get (which would 4xx).
+func TestReconcileStale3DSOrders_SkipsEmptyPaymentIntentID(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	order := seedRequiresActionOrder(t, user.ID, "pi_will_be_blanked",
+		time.Now().Add(-1*time.Hour))
+	if err := db.Model(&order).UpdateColumn("stripe_payment_id", "").Error; err != nil {
+		t.Fatalf("blank PI id: %v", err)
+	}
+
+	called := false
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(_ string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		called = true
+		return &stripe.PaymentIntent{Status: stripe.PaymentIntentStatusRequiresPaymentMethod}, nil
+	}
+
+	missing := middleware.Abandoned3DSSweepCounter().WithLabelValues("missing_pi")
+	before := testutil.ToFloat64(missing)
+
+	ReconcileStale3DSOrders(context.Background(), 30*time.Minute)
+
+	if called {
+		t.Fatalf("stripe Get called for empty-PI row")
+	}
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("empty-PI guard must leave status alone; got %q", reloaded.Status)
+	}
+	if got := testutil.ToFloat64(missing) - before; got != 1 {
+		t.Fatalf("want 1 missing_pi increment, got %v", got)
+	}
+}
+
+// TestReconcileStale3DSOrders_BailsMidLoopOnCancel verifies the per-iteration
+// ctx.Err() check stops the sweep once the supervising context cancels, so a
+// SIGTERM during a large stale-3DS batch does not block the binary past the
+// 30s graceful-shutdown window in api/main.go
+func TestReconcileStale3DSOrders_BailsMidLoopOnCancel(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	audit.SetDB(db)
+	defer audit.SetDB(nil)
+
+	seedRequiresActionOrder(t, user.ID, "pi_first", time.Now().Add(-1*time.Hour))
+	seedRequiresActionOrder(t, user.ID, "pi_second", time.Now().Add(-1*time.Hour))
+
+	ctx, cancel := context.WithCancel(context.Background())
+	defer cancel()
+
+	calls := 0
+	orig := paymentIntentGetFn
+	defer func() { paymentIntentGetFn = orig }()
+	paymentIntentGetFn = func(id string, _ *stripe.PaymentIntentParams) (*stripe.PaymentIntent, error) {
+		calls++
+		if calls == 1 {
+			cancel()
+		}
+		return &stripe.PaymentIntent{
+			ID:     id,
+			Status: stripe.PaymentIntentStatusRequiresPaymentMethod,
+		}, nil
+	}
+	ReconcileStale3DSOrders(ctx, 30*time.Minute)
+
+	if calls != 1 {
+		t.Fatalf("want exactly 1 stripe Get call (loop bails before row 2); got %d", calls)
+	}
+	var stillPending int64
+	if err := db.Model(&models.Order{}).Where("status = ?", models.OrderStatusRequiresAction).Count(&stillPending).Error; err != nil {
+		t.Fatalf("count requires_action rows: %v", err)
+	}
+	if stillPending < 1 {
+		t.Fatalf("want at least 1 row left in requires_action after mid-loop cancel; got %d", stillPending)
+	}
+}
+
+// seedRequiresActionOrder inserts a card + order pair in the requires_action
+// state. updatedAt is forced via UpdateColumn so GORM's auto-stamping of
+// UpdatedAt on Create does not bump the row out of the sweep predicate.
+func seedRequiresActionOrder(t *testing.T, userID uint, piID string, updatedAt time.Time) models.Order {
+	t.Helper()
+	db := database.GetDB()
+	card := models.Card{
+		UserID:          userID,
+		StripePaymentID: "pm_test_" + piID,
+		Last4:           "4242", Brand: "Visa",
+		ExpMonth: 12, ExpYear: 2030,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+	order := models.Order{
+		UserID: userID, CardID: card.ID,
+		StripePaymentID: piID,
+		Status:          models.OrderStatusRequiresAction,
+		Subtotal:        500, Total: 500,
+		ShippingName: "Test", ShippingStreet: "1 Main St",
+		ShippingCity: "PDX", ShippingState: "OR",
+		ShippingZip: "97201", ShippingCountry: "US",
+	}
+	if err := db.Create(&order).Error; err != nil {
+		t.Fatalf("seed order: %v", err)
+	}
+	if err := db.Model(&order).UpdateColumn("updated_at", updatedAt).Error; err != nil {
+		t.Fatalf("backdate updated_at: %v", err)
+	}
+	return order
+}
+
+// TestReconcilePayRedirects_DeleteExpiredKeepsLive verifies the predicate
+// boundary: a row past ExpiresAt is hard-deleted while a row whose ExpiresAt
+// is still in the future survives. Seeding both sides through GORM keeps the
+// stored timestamp format identical to the one the sweep binds for time.Now(),
+// so the comparison is exercised exactly as it runs in production.
+func TestReconcilePayRedirects_DeleteExpiredKeepsLive(t *testing.T) {
+	testDB := setupTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+
+	now := time.Now()
+	expired := models.PayRedirect{
+		Token:     "tok_expired",
+		URL:       "https://example.test/expired",
+		Purpose:   models.RedirectPurposeCheckout3DS,
+		CreatedAt: now.Add(-20 * time.Minute),
+		ExpiresAt: now.Add(-10 * time.Minute),
+	}
+
+	live := models.PayRedirect{
+		Token:     "tok_live",
+		URL:       "https://example.test/live",
+		Purpose:   models.RedirectPurposeAddCard,
+		CreatedAt: now,
+		ExpiresAt: now.Add(10 * time.Minute),
+	}
+	if err := db.Create(&expired).Error; err != nil {
+		t.Fatalf("seed expired: %v", err)
+	}
+	if err := db.Create(&live).Error; err != nil {
+		t.Fatalf("seed live: %v", err)
+	}
+
+	ReconcilePayRedirects(context.Background())
+
+	var remaining []models.PayRedirect
+	if err := db.Find(&remaining).Error; err != nil {
+		t.Fatalf("list remaining: %v", err)
+	}
+	if len(remaining) != 1 {
+		t.Fatalf("want 1 row remaining, got %d", len(remaining))
+	}
+	if remaining[0].Token != "tok_live" {
+		t.Fatalf("wrong row survived: want tok_live, got %q", remaining[0].Token)
+	}
+}
+
+func TestReconcilePayRedirects_NoExpiredIsNoOp(t *testing.T) {
+	testDB := setupTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+
+	live := models.PayRedirect{
+		Token:     "tok_live_only",
+		URL:       "https://example.test/live",
+		Purpose:   models.RedirectPurposeCheckout3DS,
+		CreatedAt: time.Now(),
+		ExpiresAt: time.Now().Add(10 * time.Minute),
+	}
+	if err := db.Create(&live).Error; err != nil {
+		t.Fatalf("seed live: %v", err)
+	}
+
+	ReconcilePayRedirects(context.Background())
+
+	var count int64
+	if err := db.Model(&models.PayRedirect{}).Count(&count).Error; err != nil {
+		t.Fatalf("count: %v", err)
+	}
+	if count != 1 {
+		t.Fatalf("want 1 row preserved, got %d", count)
+	}
+}

api/handlers/slack.go

@@ -0,0 +1,280 @@
+package handlers
+
+import (
+	"bytes"
+	"context"
+	"crypto/hmac"
+	"crypto/sha256"
+	"encoding/hex"
+	"encoding/json"
+	"fmt"
+	"io"
+	"log/slog"
+	"net/http"
+	"net/url"
+	"os"
+	"strconv"
+	"strings"
+	"terminalShop/pkg/audit"
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+	"terminalShop/pkg/notify"
+	"terminalShop/pkg/utils"
+	"time"
+)
+
+type SlackHandler struct {
+	signingSecret string
+	adminKey      string
+	apiPort       string
+	shippoSecret  string
+	httpClient    *http.Client
+}
+
+func NewSlackHandler(signingSecret, adminKey, apiPort, shippoWebhookSecret string) *SlackHandler {
+	return &SlackHandler{
+		signingSecret: signingSecret,
+		adminKey:      adminKey,
+		apiPort:       apiPort,
+		shippoSecret:  shippoWebhookSecret,
+		httpClient:    &http.Client{Timeout: 30 * time.Second},
+	}
+}
+
+type slackAction struct {
+	ActionID string `json:"action_id"`
+	Value    string `json:"value"`
+}
+
+type slackInteractivePayload struct {
+	Type        string        `json:"type"`
+	ResponseURL string        `json:"response_url"`
+	Actions     []slackAction `json:"actions"`
+	User        struct {
+		ID       string `json:"id"`
+		Username string `json:"username"`
+	} `json:"user"`
+}
+
+func (h *SlackHandler) HandleInteractivity(w http.ResponseWriter, r *http.Request) {
+	if h.signingSecret == "" {
+		utils.RespondError(w, http.StatusServiceUnavailable, "SLACK_NOT_CONFIGURED", "slack signing secret not set", nil)
+		return
+	}
+
+	body, err := io.ReadAll(io.LimitReader(r.Body, 1<<20))
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "READ_FAILED", "could not read body", nil)
+		return
+	}
+
+	if !h.verifySignature(r, body) {
+		utils.RespondError(w, http.StatusUnauthorized, "INVALID_SIGNATURE", "slack signature mismatch", nil)
+		return
+	}
+
+	form, err := url.ParseQuery(string(body))
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "BAD_FORM", "could not parse form body", nil)
+		return
+	}
+	rawPayload := form.Get("payload")
+	if rawPayload == "" {
+		utils.RespondError(w, http.StatusBadRequest, "MISSING_PAYLOAD", "no payload field", nil)
+		return
+	}
+
+	var p slackInteractivePayload
+	if err := json.Unmarshal([]byte(rawPayload), &p); err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "BAD_JSON_PAYLOAD", "could not parse payload", nil)
+		return
+	}
+
+	if len(p.Actions) == 0 {
+		w.WriteHeader(http.StatusOK)
+		return
+	}
+	action := p.Actions[0]
+
+	w.WriteHeader(http.StatusOK)
+
+	go h.dispatch(action, p)
+}
+
+func (h *SlackHandler) dispatch(action slackAction, p slackInteractivePayload) {
+	switch action.ActionID {
+	case "buy_label":
+		h.handleBuyLabel(action.Value, p)
+	case "mark_pre_transit":
+		h.handleMarkStatus(action.Value, p, "PRE_TRANSIT")
+	case "mark_in_transit":
+		h.handleMarkStatus(action.Value, p, "TRANSIT")
+	case "mark_delivered":
+		h.handleMarkStatus(action.Value, p, "DELIVERED")
+	default:
+		slog.Warn("slack interactivity: unknown action", "action_id", action.ActionID)
+	}
+}
+
+func (h *SlackHandler) handleBuyLabel(orderIDStr string, p slackInteractivePayload) {
+	orderID64, err := strconv.ParseUint(orderIDStr, 10, 32)
+	if err != nil {
+		slog.Warn("slack buy_label: invalid order id", "value", orderIDStr)
+		return
+	}
+	orderID := uint(orderID64)
+
+	url := fmt.Sprintf("http://localhost:%s/api/v1/orders/%d/label", h.apiPort, orderID)
+	req, _ := http.NewRequestWithContext(context.Background(), http.MethodPost, url, nil)
+	req.Header.Set("X-Admin-Key", h.adminKey)
+
+	resp, err := h.httpClient.Do(req)
+	if err != nil {
+		_ = notify.SlackPostToOrderThread(orderID, fmt.Sprintf(":x: Label purchase failed: %v", err))
+		return
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	var result struct {
+		Data struct {
+			TrackingNumber string `json:"tracking_number"`
+			Carrier        string `json:"carrier"`
+			LabelURL       string `json:"label_url"`
+			CostCents      int    `json:"cost_cents"`
+		} `json:"data"`
+		Error struct {
+			Code    string `json:"code"`
+			Message string `json:"message"`
+		} `json:"error"`
+	}
+	bodyBytes, _ := io.ReadAll(resp.Body)
+	_ = json.Unmarshal(bodyBytes, &result)
+
+	if resp.StatusCode >= 300 {
+		_ = notify.SlackPostToOrderThread(orderID, fmt.Sprintf(":x: Label purchase failed: `%s` %s", result.Error.Code, result.Error.Message))
+		return
+	}
+
+	notify.SlackPostLabelPurchased(orderID, result.Data.LabelURL, result.Data.CostCents)
+
+}
+
+func (h *SlackHandler) handleMarkStatus(orderIDStr string, p slackInteractivePayload, status string) {
+	orderID64, err := strconv.ParseUint(orderIDStr, 10, 32)
+	if err != nil {
+		slog.Warn("slack mark_status: invalid order id", "value", orderIDStr)
+		return
+	}
+	orderID := uint(orderID64)
+
+	var order models.Order
+	if err := database.GetDB().Select("id", "tracking_number", "carrier").Where("id = ?", orderID).First(&order).Error; err != nil {
+		slog.Warn("slack mark_status: order lookup failed", "order_id", orderID, "error", err)
+		return
+	}
+	if order.TrackingNumber == "" {
+		_ = notify.SlackPostToOrderThread(orderID, ":x: Cannot mark status, the order has no tracking number yet.")
+		return
+	}
+
+	detail := defaultDetailFor(status)
+	payload := map[string]any{
+		"event": "track_updated",
+		"data": map[string]any{
+			"tracking_number": order.TrackingNumber,
+			"carrier":         strings.ToLower(order.Carrier),
+			"tracking_status": map[string]any{
+				"status":         status,
+				"status_date":    time.Now().UTC().Format(time.RFC3339),
+				"status_details": detail,
+			},
+		},
+	}
+	body, _ := json.Marshal(payload)
+
+	webhookURL := fmt.Sprintf("http://localhost:%s/api/v1/webhooks/shippo?token=%s", h.apiPort, url.QueryEscape(h.shippoSecret))
+	req, _ := http.NewRequestWithContext(context.Background(), http.MethodPost, webhookURL, bytes.NewReader(body))
+	req.Header.Set("Content-Type", "application/json")
+
+	resp, err := h.httpClient.Do(req)
+	if err != nil {
+		_ = notify.SlackPostToOrderThread(orderID, fmt.Sprintf(":x: Mark %s failed: %v", status, err))
+		return
+	}
+	defer func() { _ = resp.Body.Close() }()
+	if resp.StatusCode >= 300 {
+		_ = notify.SlackPostToOrderThread(orderID, fmt.Sprintf(":x: Mark %s failed (HTTP %d)", status, resp.StatusCode))
+		return
+	}
+
+	audit.TrackingMarkedManually(orderID, status, p.User.Username)
+
+	h.editClearActions(p.ResponseURL, status, p.User.Username)
+}
+
+func defaultDetailFor(status string) string {
+	switch status {
+	case "PRE_TRANSIT":
+		return "Marked pre-transit by operator"
+	case "TRANSIT":
+		return "Marked transit by operator"
+	case "DELIVERED":
+		return "Marked delivered by operator"
+	}
+	return "Marked by operator"
+}
+
+func (h *SlackHandler) editClearActions(responseURL, status, actor string) {
+	if responseURL == "" {
+		return
+	}
+	stamp := fmt.Sprintf(":white_check_mark: Marked %s by @%s at %s", strings.ToLower(status), actor, time.Now().UTC().Format("15:04 MST"))
+	body, _ := json.Marshal(map[string]any{
+		"replace_original": true,
+		"text":             stamp,
+		"blocks": []map[string]any{
+			{"type": "context", "elements": []map[string]any{
+				{"type": "mrkdwn", "text": stamp},
+			}},
+		},
+	})
+	req, _ := http.NewRequestWithContext(context.Background(), http.MethodPost, responseURL, bytes.NewReader(body))
+	req.Header.Set("Content-Type", "application/json")
+	resp, err := h.httpClient.Do(req)
+	if err != nil {
+		slog.Warn("slack mark_status: response_url edit failed", "error", err)
+		return
+	}
+	_ = resp.Body.Close()
+}
+
+func (h *SlackHandler) verifySignature(r *http.Request, body []byte) bool {
+	tsHeader := r.Header.Get("X-Slack-Request-Timestamp")
+	sigHeader := r.Header.Get("X-Slack-Signature")
+	if tsHeader == "" || sigHeader == "" {
+		return false
+	}
+
+	ts, err := strconv.ParseInt(tsHeader, 10, 64)
+	if err != nil {
+		return false
+	}
+	if abs(time.Now().Unix()-ts) > 60*5 {
+		return false
+	}
+
+	mac := hmac.New(sha256.New, []byte(h.signingSecret))
+	_, _ = fmt.Fprintf(mac, "v0:%d:%s", ts, body)
+	expected := "v0=" + hex.EncodeToString(mac.Sum(nil))
+
+	return hmac.Equal([]byte(expected), []byte(sigHeader))
+}
+
+func abs(x int64) int64 {
+	if x < 0 {
+		return -x
+	}
+	return x
+}
+
+var _ = os.Getenv

api/handlers/ssh_keys.go

@@ -1,58 +0,0 @@
-package handlers
-
-import (
-	"net/http"
-	"strconv"
-	"terminalShop/api/middleware"
-	"terminalShop/pkg/database"
-	"terminalShop/pkg/models"
-	"terminalShop/pkg/utils"
-
-	"github.com/go-chi/chi/v5"
-)
-
-type SSHKeyHandler struct{}
-
-func NewSSHKeyHandler() *SSHKeyHandler {
-	return &SSHKeyHandler{}
-}
-
-// GetSSHKeys returns all ssh keys for the authenticated user.
-func (h *SSHKeyHandler) GetSSHKeys(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
-	userID := middleware.UserIDFromContext(r.Context())
-
-	var keys []models.SSHKey
-	db.Where("user_id = ?", userID).Order("created_at ASC").Find(&keys)
-
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
-		"ssh_keys": keys,
-	})
-}
-
-// DeleteSSHKeys removes one of the users ssh keys by ID
-func (h *SSHKeyHandler) DeleteSSHKeys(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
-	userID := middleware.UserIDFromContext(r.Context())
-
-	idStr := chi.URLParam(r, "id")
-	id, err := strconv.ParseUint(idStr, 10, 32)
-	if err != nil {
-		utils.RespondError(w, http.StatusBadRequest, "INVALID_ID", "invalid ssh key id", nil)
-		return
-	}
-
-	var key models.SSHKey
-	if err := db.Where("id = ? AND user_id = ?", id, userID).First(&key).Error; err != nil {
-		utils.RespondError(w, http.StatusNotFound, "SSH_KEY_NOT_FOUND", "ssh key not found", nil)
-		return
-	}
-	if err := db.Delete(&key).Error; err != nil {
-		utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to delete ssh key", nil)
-		return
-	}
-
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
-		"message": "ssh key deleted",
-	})
-}

api/handlers/tracking.go

@@ -0,0 +1,33 @@
+package handlers
+
+import (
+	"net/http"
+	"strconv"
+
+	"github.com/go-chi/chi/v5"
+
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+)
+
+// TrackingRedirect resolves an order ID and 302s to the carrier's tracking URL.
+// Public (no auth) so the URL stays short enough to copy from any TUI width.
+func TrackingRedirect(w http.ResponseWriter, r *http.Request) {
+	idStr := chi.URLParam(r, "id")
+	id, err := strconv.ParseUint(idStr, 10, 32)
+	if err != nil {
+		http.Error(w, "bad order id", http.StatusBadRequest)
+		return
+	}
+
+	var order models.Order
+	if err := database.GetDB().Select("tracking_url").Where("id = ?", uint(id)).First(&order).Error; err != nil {
+		http.NotFound(w, r)
+		return
+	}
+	if order.TrackingURL == "" {
+		http.NotFound(w, r)
+		return
+	}
+	http.Redirect(w, r, order.TrackingURL, http.StatusFound)
+}

api/handlers/view.go

@@ -2,13 +2,17 @@ package handlers
 
 import (
 	"net/http"
+	"time"
 
 	"terminalShop/api/middleware"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
 	"terminalShop/pkg/utils"
+
+	"gorm.io/gorm"
 )
 
+// ViewHandler handles bulk TUI bootstrap data
 type ViewHandler struct{}
 
 func NewViewHandler() *ViewHandler {
@@ -16,7 +20,7 @@ func NewViewHandler() *ViewHandler {
 }
 
 func (h *ViewHandler) GetViewInit(w http.ResponseWriter, r *http.Request) {
-	db := database.GetDB()
+	db := database.GetDB().WithContext(r.Context())
 	userID := middleware.UserIDFromContext(r.Context())
 
 	var user models.User
@@ -35,25 +39,27 @@ func (h *ViewHandler) GetViewInit(w http.ResponseWriter, r *http.Request) {
 	db.Where("user_id = ?", userID).Find(&addresses)
 
 	var cards []models.Card
-	db.Where("user_id = ?", userID).Find(&cards)
-
-	var sshKeys []models.SSHKey
-	db.Where("user_id = ?", userID).Order("created_at ASC").Find(&sshKeys)
+	db.Where(
+		"user_id = ? AND (storage_expires_at IS NULL OR storage_expires_at > ?)",
+		userID, time.Now(),
+	).Order("is_default DESC, created_at DESC").Find(&cards)
 
 	var orders []models.Order
-	db.Where("user_id = ?", userID).Preload("Items").Order("created_at desc").Find(&orders)
+	db.Where("user_id = ?", userID).
+		Preload("Items").
+		Preload("Events", func(tx *gorm.DB) *gorm.DB { return tx.Order("created_at ASC") }).
+		Order("created_at DESC").Find(&orders)
 	var cartItems []models.CartItem
 	if cart.ID != 0 {
 		db.Where("cart_id = ? AND quantity > 0", cart.ID).Preload("Coffee").Find(&cartItems)
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"user":      user.ToPublic(),
 		"products":  products,
 		"cart":      cartItems,
 		"addresses": addresses,
 		"cards":     cards,
-		"ssh_keys":  sshKeys,
 		"orders":    orders,
 	})
 }

api/handlers/view_test.go

@@ -0,0 +1,70 @@
+package handlers
+
+import (
+	"encoding/json"
+	"net/http"
+	"net/http/httptest"
+	"os"
+	"testing"
+	"time"
+
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+)
+
+// TestGetViewInit_FiltersExpiredCardsAndOrders drives the WHERE + ORDER BY
+// clauses in GetViewInit. a column-name typo in either clause (e.g.
+// id_default instead of is_default) surfaces here as a sqlite error
+func TestGetViewInit_FiltersExpiredCardsAndOrders(t *testing.T) {
+	testDB, user := setupCardsExpireTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	db := database.GetDB()
+	now := time.Now()
+	past := now.Add(-1 * time.Hour)
+	future := now.Add((24 * time.Hour))
+
+	expired := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_expired", Last4: "1111",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &past,
+	}
+	freshDefault := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_fresh_d", Last4: "2222",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &future,
+		IsDefault: true,
+	}
+	freshOther := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_fresh_o", Last4: "3333",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &future,
+	}
+	for _, card := range []*models.Card{&expired, &freshDefault, &freshOther} {
+		if err := db.Create(card).Error; err != nil {
+			t.Fatalf("seed card: %v", err)
+		}
+	}
+
+	handler := NewViewHandler()
+	req := authRequest("GET", "/api/v1/view/init", nil, user.ID)
+	w := httptest.NewRecorder()
+	handler.GetViewInit(w, req)
+
+	if w.Code != http.StatusOK {
+		t.Fatalf("GetViewInit status %d, body: %s", w.Code, w.Body.String())
+	}
+
+	var resp struct {
+		Data struct {
+			Cards []models.Card `json:"cards"`
+		} `json:"data"`
+	}
+	if err := json.NewDecoder(w.Body).Decode(&resp); err != nil {
+		t.Fatalf("decode: %v", err)
+	}
+	if len(resp.Data.Cards) != 2 {
+		t.Fatalf("want 2 visible cards, got %d", len(resp.Data.Cards))
+	}
+	if resp.Data.Cards[0].ID != freshDefault.ID {
+		t.Fatalf("default card should sort first, got id=%d (want %d)", resp.Data.Cards[0].ID, freshDefault.ID)
+	}
+}

api/handlers/webhook.go

@@ -1,11 +1,15 @@
 package handlers
 
 import (
+	"context"
 	"encoding/json"
 	"fmt"
 	"io"
-	"log"
+	"log/slog"
 	"net/http"
+	"os"
+	"strings"
+	"time"
 
 	"github.com/stripe/stripe-go/v78"
 	"github.com/stripe/stripe-go/v78/paymentmethod"
@@ -16,18 +20,22 @@ import (
 	"terminalShop/pkg/audit"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
+	"terminalShop/pkg/notify"
 	"terminalShop/pkg/utils"
 )
 
+func webhookLog() *slog.Logger { return slog.With("component", "webhook") }
+
 // WebhookHandler handles inbound Stripe webhook events.
 type WebhookHandler struct {
 	webhookSecret string
-	stripeKey     string
+	shippoSecret  string
 }
 
-// NewWebhookHandler creates a new webhook handler.
-func NewWebhookHandler(webhookSecret string, stripeKey string) *WebhookHandler {
-	return &WebhookHandler{webhookSecret: webhookSecret, stripeKey: stripeKey}
+// NewWebhookHandler creates a new webhook handler. Stripe credentials are
+// wired once at startup via stripe.Key in api/main.go.
+func NewWebhookHandler(webhookSecret, shippoSecret string) *WebhookHandler {
+	return &WebhookHandler{webhookSecret: webhookSecret, shippoSecret: shippoSecret}
 }
 
 // HandleStripe validates the Stripe signature and routes the event.
@@ -45,14 +53,23 @@ func (h *WebhookHandler) HandleStripe(w http.ResponseWriter, r *http.Request) {
 
 	// Verify the Stripe signature. Reject anything that doesn't match.
 	if h.webhookSecret == "" {
-		// No secret configured — log a loud warning but still process in dev.
-		log.Println("WARNING: STRIPE_WEBHOOK_SECRET is not set; skipping signature verification")
+		// Fail closed in production. config.validate() requires STRIPE_WEBHOOK_SECRET
+		// in production, so the server should never boot into this state; this is
+		// defense in depth against a misconfigured deploy. Mirrors the Shippo and
+		// Slack handlers, which already refuse to run without their secret.
+		if os.Getenv("ENVIRONMENT") == "production" {
+			webhookLog().Error("stripe webhook secret not set in production; refusing to process event")
+			utils.RespondError(w, http.StatusServiceUnavailable, "WEBHOOK_NOT_CONFIGURED", "webhook verification not configured", nil)
+			return
+		}
+		// Development only; warn loudly but still process so local testing works.
+		webhookLog().Warn("stripe webhook secret not set; skipping signature verification (development only)")
 	} else {
 		sig := r.Header.Get("Stripe-Signature")
 		if _, err := webhook.ConstructEventWithOptions(body, sig, h.webhookSecret, webhook.ConstructEventOptions{
 			IgnoreAPIVersionMismatch: true,
 		}); err != nil {
-			log.Printf("[webhook] signature verification failed: %v", err)
+			webhookLog().Warn("signature verification failed", "error", err)
 			utils.RespondError(w, http.StatusUnauthorized, "INVALID_SIGNATURE", "webhook signature verification failed", nil)
 			return
 		}
@@ -67,35 +84,35 @@ func (h *WebhookHandler) HandleStripe(w http.ResponseWriter, r *http.Request) {
 	switch event.Type {
 
 	case "checkout.session.completed":
-		h.handleCheckoutSessionCompleted(event)
+		h.handleCheckoutSessionCompleted(r.Context(), event)
 
 	// payment_intent.succeeded fires when a charge completes asynchronously
 	// (e.g. 3DS, bank redirects). For confirm=true intents this is normally
 	// already handled by ConvertCart, but the webhook is the authoritative source.
 	case "payment_intent.succeeded":
-		h.handlePaymentIntentSucceeded(event)
+		h.handlePaymentIntentSucceeded(r.Context(), event)
 
 	// payment_intent.payment_failed fires when a payment fails after initial
 	// confirmation (e.g. bank decline on a deferred 3DS flow).
 	case "payment_intent.payment_failed":
-		h.handlePaymentIntentFailed(event)
+		h.handlePaymentIntentFailed(r.Context(), event)
 
 	// Sync local card state when Stripe's side changes.
 	case "payment_method.attached",
 		"payment_method.detached",
 		"payment_method.updated":
 		// Handled by the reconcile job and direct API calls; log only.
-		log.Printf("[webhook] %s received for payment method", event.Type)
+		webhookLog().Info("payment method event received", "event_type", string(event.Type))
 	}
 
 	// Always return 200 so Stripe doesn't retry.
 	w.WriteHeader(http.StatusOK)
 }
 
-func (h *WebhookHandler) handlePaymentIntentSucceeded(event stripe.Event) {
+func (h *WebhookHandler) handlePaymentIntentSucceeded(ctx context.Context, event stripe.Event) {
 	var pi stripe.PaymentIntent
 	if err := json.Unmarshal(event.Data.Raw, &pi); err != nil {
-		log.Printf("[webhook] failed to unmarshal payment_intent: %v", err)
+		webhookLog().Error("failed to unmarshal payment_intent", "error", err, "event", "payment_intent.succeeded")
 		return
 	}
 
@@ -105,10 +122,10 @@ func (h *WebhookHandler) handlePaymentIntentSucceeded(event stripe.Event) {
 		return
 	}
 
-	db := database.GetDB()
+	db := database.GetDB().WithContext(ctx)
 	var order models.Order
-	if err := db.Where("id = ?", orderIDStr).First(&order).Error; err != nil {
-		log.Printf("[webhook] order %s not found for pi %s", orderIDStr, pi.ID)
+	if err := db.Preload("Items").Where("id = ?", orderIDStr).First(&order).Error; err != nil {
+		webhookLog().Warn("order not found for payment intent", "order_id", orderIDStr, "pi", pi.ID)
 		return
 	}
 
@@ -117,8 +134,22 @@ func (h *WebhookHandler) handlePaymentIntentSucceeded(event stripe.Event) {
 		return
 	}
 
+	// Defense in depth: even behind a valid signature, refuse to mark an order
+	// paid unless the PaymentIntent's amount and currency match what we charged.
+	// Under ConvertCart these always match (Amount == order.Total at creation), so
+	// a mismatch means a malformed or unexpected event we should not trust.
+	if pi.Amount != int64(order.Total) {
+		webhookLog().Error("payment intent amount mismatch; refusing to mark paid", "order_id", orderIDStr, "pi", pi.ID, "pi_amount", pi.Amount, "order_total", order.Total)
+		return
+	}
+	if pi.Currency != "" && pi.Currency != stripe.CurrencyUSD {
+		webhookLog().Error("payment intent currency mismatch; refusing to mark paid",
+			"order_id", orderIDStr, "pi", pi.ID, "currency", string(pi.Currency))
+		return
+	}
+
 	txErr := db.Transaction(func(tx *gorm.DB) error {
-		if err := tx.Model(&order).Updates(map[string]interface{}{
+		if err := tx.Model(&order).Updates(map[string]any{
 			"status":            models.OrderStatusPaid,
 			"stripe_payment_id": pi.ID,
 		}).Error; err != nil {
@@ -132,24 +163,32 @@ func (h *WebhookHandler) handlePaymentIntentSucceeded(event stripe.Event) {
 		if err := tx.Where("cart_id = ?", cart.ID).Delete(&models.CartItem{}).Error; err != nil {
 			return fmt.Errorf("failed to delete cart item: %w", err)
 		}
-		return tx.Model(&cart).Updates(map[string]interface{}{
+		return tx.Model(&cart).Updates(map[string]any{
 			"address_id": nil,
 			"card_id":    nil,
 		}).Error
 	})
 	if txErr != nil {
-		log.Printf("[webhook] failed to record paid status for order %s (pi=%s): %v", orderIDStr, pi.ID, txErr)
+		webhookLog().Error("failed to record paid status",
+			"order_id", orderIDStr, "pi", pi.ID, "error", txErr)
 		return
 	}
 
+	if order.CardID != 0 {
+		if err := refreshCardStorageTTL(db, order.CardID, time.Now()); err != nil {
+			webhookLog().Warn("failed to refresh card storage ttl", "card_id", order.CardID, "error", err)
+		}
+	}
+
 	audit.OrderPaid(order.UserID, order.ID, int(pi.Amount), pi.ID)
-	log.Printf("[webhook] order %s marked paid via payment_intent.succeeded (pi=%s)", orderIDStr, pi.ID)
+	go notify.SlackOrderPaid(&order)
+	webhookLog().Info("order marked paid", "order_id", orderIDStr, "pi", pi.ID)
 }
 
-func (h *WebhookHandler) handlePaymentIntentFailed(event stripe.Event) {
+func (h *WebhookHandler) handlePaymentIntentFailed(ctx context.Context, event stripe.Event) {
 	var pi stripe.PaymentIntent
 	if err := json.Unmarshal(event.Data.Raw, &pi); err != nil {
-		log.Printf("[webhook] failed to unmarshal payment_intent: %v", err)
+		webhookLog().Error("failed to unmarshal payment_intent", "error", err, "event", "payment_intent.payment_failed")
 		return
 	}
 
@@ -158,23 +197,33 @@ func (h *WebhookHandler) handlePaymentIntentFailed(event stripe.Event) {
 		return
 	}
 
-	db := database.GetDB()
-	if err := db.Model(&models.Order{}).Where("id = ? AND status = ?", orderIDStr, models.OrderStatusPending).
+	// authentication_required is recoverable — the cart handler re-confirms the
+	// PI on-session and the customer completes 3DS via redirect. Marking the
+	// order failed here would race with the recovery path and surface a
+	// momentarily-broken state in the TUI.
+	if pi.LastPaymentError != nil && string(pi.LastPaymentError.Code) == "authentication_required" {
+		webhookLog().Info("ignoring authentication_required payment_failed; handled via 3ds redirect",
+			"order_id", orderIDStr, "pi", pi.ID)
+		return
+	}
+
+	db := database.GetDB().WithContext(ctx)
+	if err := db.Model(&models.Order{}).Where("id = ? AND status IN (?, ?)", orderIDStr, models.OrderStatusPending, models.OrderStatusRequiresAction).
 		Update("status", models.OrderStatusFailed).Error; err != nil {
-		log.Printf("[webhook] failed to mark order %s as failed: %v", orderIDStr, err)
+		webhookLog().Error("failed to mark order failed", "order_id", orderIDStr, "error", err)
 	}
 
 	errMsg := "unknown"
 	if pi.LastPaymentError != nil {
 		errMsg = pi.LastPaymentError.Msg
 	}
-	log.Printf("[webhook] payment failed for order %s (pi=%s): %s", orderIDStr, pi.ID, errMsg)
+	webhookLog().Warn("payment failed", "order_id", orderIDStr, "pi", pi.ID, "reason", errMsg)
 }
 
-func (h *WebhookHandler) handleCheckoutSessionCompleted(event stripe.Event) {
+func (h *WebhookHandler) handleCheckoutSessionCompleted(ctx context.Context, event stripe.Event) {
 	var sess stripe.CheckoutSession
 	if err := json.Unmarshal(event.Data.Raw, &sess); err != nil {
-		log.Printf("[webhook] failed to unmarshal checkout session: %v", err)
+		webhookLog().Error("failed to unmarshal checkout session", "error", err)
 		return
 	}
 
@@ -183,42 +232,72 @@ func (h *WebhookHandler) handleCheckoutSessionCompleted(event stripe.Event) {
 	}
 
 	if sess.SetupIntent == nil || sess.Customer == nil {
-		log.Printf("[webhook] checkout session missing setup_intent or customer")
+		webhookLog().Warn("checkout session missing setup_intent or customer")
 		return
 	}
 
-	stripe.Key = h.stripeKey
-
 	si, err := setupintent.Get(sess.SetupIntent.ID, nil)
 	if err != nil {
-		log.Printf("[webhook] failed to get setup intent %s: %v", sess.SetupIntent.ID, err)
+		webhookLog().Error("failed to get setup intent", "setup_intent", sess.SetupIntent.ID, "error", err)
 		return
 	}
 
 	if si.PaymentMethod == nil {
-		log.Printf("[webhook] setup intent %s has no payment method", si.ID)
+		webhookLog().Warn("setup intent has no payment method", "setup_intent", si.ID)
 		return
 	}
 
 	pm, err := paymentmethod.Get(si.PaymentMethod.ID, nil)
 	if err != nil {
-		log.Printf("[webhook] failed to get payment method %s: %v", si.PaymentMethod.ID, err)
+		webhookLog().Error("failed to get payment method", "payment_method", si.PaymentMethod.ID, "error", err)
 		return
 	}
 
-	db := database.GetDB()
+	db := database.GetDB().WithContext(ctx)
 	var user models.User
 	if err := db.Where("stripe_customer_id = ?", sess.Customer.ID).First(&user).Error; err != nil {
-		log.Printf("[webhook] user not found for customer %s: %v", sess.Customer.ID, err)
+		webhookLog().Warn("user not found for customer", "customer", sess.Customer.ID, "error", err)
 		return
 	}
 
-	// Idempotency: skip if this payment method is already saved.
+	// Idempotency: skip if this exact PaymentMethod is already in use
 	var existing models.Card
 	if err := db.Where("user_id = ? AND stripe_payment_id = ?", user.ID, pm.ID).First(&existing).Error; err == nil {
 		return
 	}
 
+	// dedup against local cards table, matching last4 + brand + expiry means
+	// the user is re-adding the same physical card. detach the new pm from
+	// stripe and skip the local insert. Local DB is the source of truth
+	// the stripe customers paymentmethods list may contain orphans from before
+	// this fix, which would cause false-positive dedup hits
+	if pm.Card != nil {
+		var dup models.Card
+		err := db.Where(
+			"user_id = ? AND last4 = ? AND brand = ? AND exp_month = ? AND exp_year = ?",
+			user.ID, pm.Card.Last4, string(pm.Card.Brand),
+			int(pm.Card.ExpMonth), int(pm.Card.ExpYear),
+		).First(&dup).Error
+		if err == nil {
+			if _, derr := paymentmethod.Detach(pm.ID, nil); derr != nil {
+				webhookLog().Warn("failed to detach duplicate pm", "user_id", user.ID, "error", derr)
+			}
+			// Bump UpdatedAt so the TUI poll signal can detect that the webhook
+			// fired even though no new row was inserted. storage_expires_at is
+			// reset because the user just re-added the card; this is a card-add
+			// path, not a payment-success refresh, so last_used_at stays as-is.
+			now := time.Now()
+			if uerr := db.Model(&dup).Updates(map[string]any{
+				"updated_at":         now,
+				"storage_expires_at": models.CardStorageExpiresAt(now),
+			}).Error; uerr != nil {
+				webhookLog().Warn("failed to bump dup card updated_at", "card_id", dup.ID, "error", uerr)
+			}
+			webhookLog().Info("skipped duplicate card via local-db match", "user_id", user.ID, "existing_card_id", dup.ID)
+			return
+		}
+	}
+
 	card := models.Card{
 		UserID:          user.ID,
 		StripePaymentID: pm.ID,
@@ -227,12 +306,178 @@ func (h *WebhookHandler) handleCheckoutSessionCompleted(event stripe.Event) {
 		ExpMonth:        int(pm.Card.ExpMonth),
 		ExpYear:         int(pm.Card.ExpYear),
 	}
+	card.InitializeStorageTTL(time.Now())
 
 	if err := db.Create(&card).Error; err != nil {
-		log.Printf("[webhook] failed to save card for user %d: %v", user.ID, err)
+		webhookLog().Error("failed to save card", "user_id", user.ID, "error", err)
 		return
 	}
 
 	audit.CardAdded(user.ID, card.ID, card.Brand, card.Last4)
-	log.Printf("[webhook] card saved via checkout.session.completed for user %d", user.ID)
+	webhookLog().Info("card saved via checkout.session.completed", "user_id", user.ID)
+}
+
+func (h *WebhookHandler) HandleShippo(w http.ResponseWriter, r *http.Request) {
+	token := r.URL.Query().Get("token")
+	if h.shippoSecret == "" || token != h.shippoSecret {
+		webhookLog().Warn("shippo webhook: token missing or invalid")
+		utils.RespondError(w, http.StatusUnauthorized, "INVALID_TOKEN", "token missing or invalid", nil)
+		return
+	}
+
+	const maxBodyBytes = 65536
+	r.Body = http.MaxBytesReader(w, r.Body, maxBodyBytes)
+	body, err := io.ReadAll(r.Body)
+	if err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "READ_ERROR", "could not read request body", nil)
+		return
+	}
+
+	var payload struct {
+		Event string `json:"event"`
+		Data  struct {
+			TrackingNumber string `json:"tracking_number"`
+			Carrier        string `json:"carrier"`
+			TrackingStatus struct {
+				Status        string    `json:"status"`
+				StatusDetails string    `json:"status_details"`
+				StatusDate    time.Time `json:"status_date"`
+			} `json:"tracking_status"`
+		} `json:"data"`
+	}
+	if err := json.Unmarshal(body, &payload); err != nil {
+		utils.RespondError(w, http.StatusBadRequest, "INVALID_JSON", "could not parse event", nil)
+		return
+	}
+
+	if payload.Event != "track_updated" {
+		webhookLog().Info("shippo webhook: ignoring no-tracking event", "event", payload.Event)
+		writeShippoResponse(w, map[string]any{
+			"received": true,
+			"skipped":  "non-tracking event",
+			"event":    payload.Event,
+		})
+		return
+	}
+
+	newStatus, known := mapShippoStatus(payload.Data.TrackingStatus.Status)
+	if !known {
+		webhookLog().Warn("shippo webhook: unrecognized status, skipping",
+			"status", payload.Data.TrackingStatus.Status,
+			"tracking_number", payload.Data.TrackingNumber)
+		writeShippoResponse(w, map[string]any{
+			"received":   true,
+			"skipped":    "unrecognized status",
+			"raw_status": payload.Data.TrackingStatus.Status,
+		})
+		return
+	}
+
+	db := database.GetDB().WithContext(r.Context())
+	var order models.Order
+	if err := db.Where("tracking_number = ?", payload.Data.TrackingNumber).First(&order).Error; err != nil {
+		webhookLog().Warn("shippo webhook: order not found",
+			"tracking_number", payload.Data.TrackingNumber)
+		writeShippoResponse(w, map[string]any{
+			"received":        true,
+			"skipped":         "order not found",
+			"tracking_number": payload.Data.TrackingNumber,
+		})
+		return
+	}
+
+	if order.TrackingStatusUpdatedAt != nil && !payload.Data.TrackingStatus.StatusDate.After(*order.TrackingStatusUpdatedAt) {
+		writeShippoResponse(w, map[string]any{
+			"received":                true,
+			"skipped":                 "stale status_date",
+			"order_id":                order.ID,
+			"current_tracking_status": string(order.TrackingStatus),
+		})
+		return
+	}
+
+	statusDate := payload.Data.TrackingStatus.StatusDate
+	previousTrackingStatus := order.TrackingStatus
+	updates := map[string]any{
+		"tracking_status":            newStatus,
+		"tracking_status_details":    payload.Data.TrackingStatus.StatusDetails,
+		"tracking_status_updated_at": &statusDate,
+	}
+	deliveredTransition := newStatus == models.TrackingStatusDelivered &&
+		order.Status != models.OrderStatusDelivered
+	if deliveredTransition {
+		updates["status"] = models.OrderStatusDelivered
+	}
+
+	if err := db.Model(&order).Updates(updates).Error; err != nil {
+		webhookLog().Error("shippo webhook: failed to persist tracking update",
+			"order_id", order.ID, "error", err)
+		utils.RespondError(w, http.StatusInternalServerError, "DB_ERROR", "failed to persist", nil)
+		return
+	}
+
+	if previousTrackingStatus != newStatus {
+		audit.TrackingUpdated(order.ID, order.Carrier, payload.Data.TrackingNumber, string(newStatus))
+		go func() {
+			_ = notify.SlackPostToOrderThread(order.ID, formatTrackingUpdate(newStatus, payload.Data.TrackingStatus.StatusDetails))
+		}()
+	}
+	if deliveredTransition {
+		audit.OrderDelivered(order.ID, payload.Data.TrackingNumber)
+	}
+	writeShippoResponse(w, map[string]any{
+		"received":                 true,
+		"order_id":                 order.ID,
+		"tracking_status":          string(newStatus),
+		"previous_tracking_status": string(previousTrackingStatus),
+		"lifecycle_status":         string(order.Status),
+		"delivered_transition":     deliveredTransition,
+		"status_details":           payload.Data.TrackingStatus.StatusDetails,
+	})
+}
+
+func formatTrackingUpdate(status models.TrackingStatus, details string) string {
+	var icon, label string
+	switch status {
+	case models.TrackingStatusPreTransit:
+		icon, label = ":label:", "Label created"
+	case models.TrackingStatusTransit:
+		icon, label = ":truck:", "In transit"
+	case models.TrackingStatusDelivered:
+		icon, label = ":white_check_mark:", "Delivered"
+	case models.TrackingStatusReturned:
+		icon, label = ":leftwards_arrow_with_hook:", "Returned to sender"
+	case models.TrackingStatusFailure:
+		icon, label = ":warning:", "Delivery exception"
+	default:
+		icon, label = ":package:", string(status)
+	}
+	if details != "" {
+		return fmt.Sprintf("%s *%s* — %s", icon, label, details)
+	}
+	return fmt.Sprintf("%s *%s*", icon, label)
+}
+
+func mapShippoStatus(s string) (models.TrackingStatus, bool) {
+	switch strings.ToUpper(strings.TrimSpace(s)) {
+	case "UNKNOWN":
+		return models.TrackingStatusUnknown, true
+	case "PRE_TRANSIT":
+		return models.TrackingStatusPreTransit, true
+	case "TRANSIT":
+		return models.TrackingStatusTransit, true
+	case "DELIVERED":
+		return models.TrackingStatusDelivered, true
+	case "RETURNED":
+		return models.TrackingStatusReturned, true
+	case "FAILURE":
+		return models.TrackingStatusFailure, true
+	}
+	return models.TrackingStatusUnknown, false
+}
+
+func writeShippoResponse(w http.ResponseWriter, payload map[string]any) {
+	w.Header().Set("Content-Type", "application/json")
+	w.WriteHeader(http.StatusOK)
+	_ = json.NewEncoder(w).Encode(payload)
 }

api/handlers/webhook_test.go

@@ -0,0 +1,259 @@
+package handlers
+
+import (
+	"context"
+	"encoding/json"
+	"fmt"
+	"os"
+	"testing"
+
+	"github.com/stripe/stripe-go/v78"
+
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+)
+
+// buildPaymentFailedEvent constructs a stripe.Event whose Data.Raw decodes to
+// a PaymentIntent referencing the given order via metadata. errCode is set on
+// last_payment_error to drive the authentication_required short-circuit
+// branch in handlePaymentIntentFailed (pass "" to omit the error block).
+func buildPaymentFailedEvent(t *testing.T, piID string, orderID uint, errCode string) stripe.Event {
+	t.Helper()
+	pi := map[string]any{
+		"id":       piID,
+		"metadata": map[string]string{"order_id": fmt.Sprintf("%d", orderID)},
+	}
+	if errCode != "" {
+		pi["last_payment_error"] = map[string]any{"code": errCode}
+	}
+	raw, err := json.Marshal(pi)
+	if err != nil {
+		t.Fatalf("marshal pi: %v", err)
+	}
+	return stripe.Event{
+		Type: "payment_intent.payment_failed",
+		Data: &stripe.EventData{Raw: raw},
+	}
+}
+
+func seedOrderForWebhook(t *testing.T, userID uint, status models.OrderStatus, piID string) models.Order {
+	t.Helper()
+	db := database.GetDB()
+	card := models.Card{
+		UserID:          userID,
+		StripePaymentID: fmt.Sprintf("pm_test_%s", piID),
+		Last4:           "4242", Brand: "Visa", ExpMonth: 12, ExpYear: 2030,
+	}
+	if err := db.Create(&card).Error; err != nil {
+		t.Fatalf("seed card: %v", err)
+	}
+	order := models.Order{
+		UserID: userID, CardID: card.ID,
+		StripePaymentID: piID,
+		Status:          status,
+		Subtotal:        500, Total: 500,
+		ShippingName: "Test", ShippingStreet: "1 Main St",
+		ShippingCity: "PDX", ShippingState: "OR",
+		ShippingZip: "97201", ShippingCountry: "US",
+	}
+	if err := db.Create(&order).Error; err != nil {
+		t.Fatalf("seed order: %v", err)
+	}
+	return order
+}
+
+// TestHandlePaymentIntentFailed_RequiresActionFlipsToFailed verifies the
+// widened predicate (IN (pending, requires_action)) catches a row in the new
+// requires_action state. Without this case, a card_declined webhook arriving
+// after respondRequiresAction wrote requires_action would leave the row
+// stuck forever.
+func TestHandlePaymentIntentFailed_RequiresActionFlipsToFailed(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	order := seedOrderForWebhook(t, user.ID, models.OrderStatusRequiresAction, "pi_test_req_action_failed")
+
+	h := NewWebhookHandler("", "")
+	evt := buildPaymentFailedEvent(t, order.StripePaymentID, order.ID, "card_declined")
+	h.handlePaymentIntentFailed(context.Background(), evt)
+
+	db := database.GetDB()
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusFailed {
+		t.Fatalf("status: want %q, got %q", models.OrderStatusFailed, reloaded.Status)
+	}
+}
+
+// TestHandlePaymentIntentFailed_RequiresActionAuthRequiredShortCircuits
+// verifies the existing short-circuit (note #3 in sca-psd2-compliance.md)
+// still fires when the row is in requires_action and the error code is
+// authentication_required. Without the short-circuit, the recovery flow
+// would race the webhook and surface a momentarily-failed state to the TUI.
+func TestHandlePaymentIntentFailed_RequiresActionAuthRequiredShortCircuits(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	order := seedOrderForWebhook(t, user.ID, models.OrderStatusRequiresAction, "pi_test_req_action_authreq")
+
+	h := NewWebhookHandler("", "")
+	evt := buildPaymentFailedEvent(t, order.StripePaymentID, order.ID, "authentication_required")
+	h.handlePaymentIntentFailed(context.Background(), evt)
+
+	db := database.GetDB()
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusRequiresAction {
+		t.Fatalf("auth_required must not flip requires_action; got %q", reloaded.Status)
+	}
+}
+
+// TestHandlePaymentIntentFailed_PendingStillFlips guards the pre-existing
+// pending -> failed transition against a regression where the widened
+// predicate accidentally dropped pending from the source set.
+func TestHandlePaymentIntentFailed_PendingStillFlips(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	order := seedOrderForWebhook(t, user.ID, models.OrderStatusPending, "pi_test_pending_failed")
+
+	h := NewWebhookHandler("", "")
+	evt := buildPaymentFailedEvent(t, order.StripePaymentID, order.ID, "card_declined")
+	h.handlePaymentIntentFailed(context.Background(), evt)
+
+	db := database.GetDB()
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusFailed {
+		t.Fatalf("status: want %q, got %q", models.OrderStatusFailed, reloaded.Status)
+	}
+}
+
+// TestHandlePaymentIntentFailed_PaidNotTouched locks the upper boundary of
+// the predicate: a paid row must NEVER be flipped to failed by a stale
+// payment_failed webhook. Without this guard, a future maintainer could
+// widen the IN clause to include paid (e.g. for some refund-retry flow)
+// and silently break idempotency.
+func TestHandlePaymentIntentFailed_PaidNotTouched(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	order := seedOrderForWebhook(t, user.ID, models.OrderStatusPaid, "pi_test_paid_untouched")
+
+	h := NewWebhookHandler("", "")
+	evt := buildPaymentFailedEvent(t, order.StripePaymentID, order.ID, "card_declined")
+	h.handlePaymentIntentFailed(context.Background(), evt)
+
+	db := database.GetDB()
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusPaid {
+		t.Fatalf("paid order was modified by payment_failed webhook: got %q", reloaded.Status)
+	}
+}
+
+// TestHandlePaymentIntentFailed_MissingMetadataNoOp covers the no-order
+// short-circuit so the test file exercises every early-return branch in
+// handlePaymentIntentFailed touched by the predicate work.
+func TestHandlePaymentIntentFailed_MissingMetadataNoOp(t *testing.T) {
+	testDB, _ := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	pi := map[string]any{"id": "pi_test_no_meta"}
+	raw, err := json.Marshal(pi)
+	if err != nil {
+		t.Fatalf("marshal pi: %v", err)
+	}
+	evt := stripe.Event{
+		Type: "payment_intent.payment_failed",
+		Data: &stripe.EventData{Raw: raw},
+	}
+
+	h := NewWebhookHandler("", "")
+	h.handlePaymentIntentFailed(context.Background(), evt) // must not panic
+}
+
+func TestHandlePaymentIntentSucceeded_RequiresActionFlipsToPaid(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	order := seedOrderForWebhook(t, user.ID, models.OrderStatusRequiresAction, "pi_test_req_action_paid")
+
+	pi := map[string]any{
+		"id":       order.StripePaymentID,
+		"amount":   order.Total,
+		"metadata": map[string]string{"order_id": fmt.Sprintf("%d", order.ID)},
+	}
+	raw, err := json.Marshal(pi)
+	if err != nil {
+		t.Fatalf("marshal pi: %v", err)
+	}
+	evt := stripe.Event{
+		Type: "payment_intent.succeeded",
+		Data: &stripe.EventData{Raw: raw},
+	}
+
+	h := NewWebhookHandler("", "")
+	h.handlePaymentIntentSucceeded(context.Background(), evt)
+
+	db := database.GetDB()
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reload order: %v", err)
+	}
+	if reloaded.Status != models.OrderStatusPaid {
+		t.Fatalf("status: want %q, got %q", models.OrderStatusPaid, reloaded.Status)
+	}
+	if reloaded.StripePaymentID != order.StripePaymentID {
+		t.Fatalf("stripe_payment_id: want %q, got %q", order.StripePaymentID, reloaded.StripePaymentID)
+	}
+}
+
+func TestHandlePaymentIntentSucceeded_AmountMismatchDoesNotPay(t *testing.T) {
+	testDB, user := setupCartTestDB(t)
+	defer func() { _ = os.Remove(testDB) }()
+	defer database.ResetForTesting()
+
+	order := seedOrderForWebhook(t, user.ID, models.OrderStatusRequiresAction, "pi_test_amount_mismatch")
+
+	// PI claims 1 cent; seed order.Total is 500.
+	pi := map[string]any{
+		"id":       order.StripePaymentID,
+		"amount":   1,
+		"metadata": map[string]string{"order_id": fmt.Sprintf("%d", order.ID)},
+	}
+	raw, err := json.Marshal(pi)
+	if err != nil {
+		t.Fatalf("marshal pi: %v", err)
+	}
+	evt := stripe.Event{
+		Type: "payment_intent.succeeded",
+		Data: &stripe.EventData{Raw: raw},
+	}
+
+	h := NewWebhookHandler("", "")
+	h.handlePaymentIntentSucceeded(context.Background(), evt)
+
+	db := database.GetDB()
+	var reloaded models.Order
+	if err := db.First(&reloaded, order.ID).Error; err != nil {
+		t.Fatalf("reloaded order: %v", err)
+	}
+	if reloaded.Status == models.OrderStatusPaid {
+		t.Fatalf("order marked paid despite amount mismatch")
+	}
+}

api/main.go

@@ -11,15 +11,24 @@ import (
 	"time"
 
 	"terminalShop/api/handlers"
+	"terminalShop/api/middleware"
 	"terminalShop/api/routes"
+	"terminalShop/pkg/audit"
 	"terminalShop/pkg/auth"
 	"terminalShop/pkg/config"
 	"terminalShop/pkg/database"
+	"terminalShop/pkg/observability"
+	"terminalShop/pkg/stripeclient"
+
+	"github.com/stripe/stripe-go/v78"
 )
 
 const version = "v0.1.0"
 
 func main() {
+	observability.InitLogger()
+	middleware.SetBuildInfo(version)
+
 	ctx, cancel := context.WithCancel(context.Background())
 	defer cancel()
 	// Load configuration
@@ -33,23 +42,44 @@ func main() {
 	if err != nil {
 		log.Fatalf("Failed to connect to database: %v", err)
 	}
-	defer database.Close()
+
+	defer func() { _ = database.Close() }()
 
 	// Run migrations
 	if err := database.Migrate(db); err != nil {
 		log.Fatalf("Failed to run migrations: %v", err)
 	}
+	audit.SetDB(db)
+
+	// wire the stripe SDK's package-level key once at startup so concurrent
+	// reconcilers and the request path don't race on stripe.Key writes.
+	// NOTE: assumes single-process — if you ever embed both the SSH and API
+	// binaries together, the last writer wins and one of them silently breaks.
+	stripe.Key = cfg.StripeSecretKey
 
 	// Seed database with initial data
 	if err := database.Seed(db); err != nil {
 		log.Fatalf("Failed to seed database: %v", err)
 	}
 
+	otlpEndpoint := os.Getenv("OTLP_ENDPOINT")
+	if otlpEndpoint == "" {
+		otlpEndpoint = "tempo:4318"
+	}
+	shutdown, err := observability.InitTracing(context.Background(), "terminalshop-api", otlpEndpoint)
+	if err != nil {
+		log.Printf("tracing init failed (non-fatal): %v", err)
+	} else {
+		defer func() { _ = shutdown(context.Background()) }()
+	}
+
+	stripeclient.InitOTel()
+
 	// Init JWT manager (same secret + duration as SSH server)
 	jwtManager := auth.NewJWTManager(cfg.JWTSecret, 30*time.Minute)
 
 	// Setup routes
-	router := routes.SetupRoutes(version, cfg.StripeSecretKey, cfg.StripeWebhookSecret, jwtManager, cfg.AuthFingerprintKey, cfg.ShippoAPIKey, cfg.BringAPIUID, cfg.BringAPIKey, cfg.AppURL)
+	router := routes.SetupRoutes(version, cfg.StripeWebhookSecret, jwtManager, cfg.AuthFingerprintKey, cfg.ShippoAPIKey, cfg.BringAPIUID, cfg.BringAPIKey, cfg.BringCustomerNumber, cfg.ShippoWebhookSecret, cfg.AppURL, cfg.SlackSigningSecret, cfg.AdminAPIKey, cfg.APIPort, cfg.MaxOrderCents)
 
 	// Create HTTP server
 	server := &http.Server{
@@ -84,7 +114,69 @@ func main() {
 		for {
 			select {
 			case <-ticker.C:
-				handlers.ReconcileOrders(cfg.StripeSecretKey)
+				handlers.ReconcileOrders(ctx)
+			case <-ctx.Done():
+				return
+			}
+		}
+	}()
+
+	go func() {
+		select {
+		case <-time.After(30 * time.Second):
+		case <-ctx.Done():
+			return
+		}
+		handlers.ReconcileUnshipped(ctx)
+		ticker := time.NewTicker(24 * time.Hour)
+		defer ticker.Stop()
+		for {
+			select {
+			case <-ticker.C:
+				handlers.ReconcileUnshipped(ctx)
+			case <-ctx.Done():
+				return
+			}
+		}
+	}()
+
+	// Sweep saved cards whose retention deadline elapsed. Read paths filter
+	// expired rows from query results, so this sweeper only drives the Stripe
+	// detach + audit + physical row delete asynchronously.
+	go func() {
+		ticker := time.NewTicker(1 * time.Hour)
+		defer ticker.Stop()
+		for {
+			select {
+			case <-ticker.C:
+				handlers.ReconcileExpiredCards(ctx)
+			case <-ctx.Done():
+				return
+			}
+		}
+	}()
+
+	go func() {
+		ticker := time.NewTicker(15 * time.Minute)
+		defer ticker.Stop()
+		threshold := time.Duration(cfg.Abandoned3DSThresholdMinutes) * time.Minute
+		for {
+			select {
+			case <-ticker.C:
+				handlers.ReconcileStale3DSOrders(ctx, threshold)
+			case <-ctx.Done():
+				return
+			}
+		}
+	}()
+
+	go func() {
+		ticker := time.NewTicker(10 * time.Minute)
+		defer ticker.Stop()
+		for {
+			select {
+			case <-ticker.C:
+				handlers.ReconcilePayRedirects(ctx)
 			case <-ctx.Done():
 				return
 			}
@@ -99,10 +191,10 @@ func main() {
 	log.Println("Server is shutting down...")
 
 	// Graceful shutdown with 30 second timeout
-	ctx, cancel = context.WithTimeout(context.Background(), 30*time.Second)
-	defer cancel()
+	shutdownCtx, shutdownCancel := context.WithTimeout(context.Background(), 30*time.Second)
+	defer shutdownCancel()
 
-	if err := server.Shutdown(ctx); err != nil {
+	if err := server.Shutdown(shutdownCtx); err != nil {
 		log.Fatalf("Server forced to shutdown: %v", err)
 	}
 

api/middleware/admin.go

@@ -0,0 +1,25 @@
+package middleware
+
+import (
+	"net/http"
+	"os"
+	"terminalShop/pkg/utils"
+)
+
+// RequireAdmin gates a handler behind X-Admin-Key matching the ADMIN_API_KEY
+// environment variable. if ADMIN_API_KEY is not set the endpoint returns 503, admin actions
+// must be explicitly enabled, never be the default option
+func RequireAdmin(next http.Handler) http.Handler {
+	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		expected := os.Getenv("ADMIN_API_KEY")
+		if expected == "" {
+			utils.RespondError(w, http.StatusServiceUnavailable, "ADMIN_DISABLED", "admin endpoints are disabled", nil)
+			return
+		}
+		if r.Header.Get("X-Admin-Key") != expected {
+			utils.RespondError(w, http.StatusUnauthorized, "UNAUTHORIZED", "invalid admin api key", nil)
+			return
+		}
+		next.ServeHTTP(w, r)
+	})
+}

api/middleware/doc.go

@@ -0,0 +1,4 @@
+// Package middleware holds the stuff that runs on every request before a
+// handler ever sees it: auth, CORS, logging, rate limiting, metrics, and a
+// recovery net for panics.
+package middleware

api/middleware/logger.go

@@ -4,16 +4,19 @@ import (
 	"log"
 	"net/http"
 	"time"
+
+	"go.opentelemetry.io/otel/trace"
 )
 
-// responseWriter wraps http.ResponseWriter to capture status code
+// responseWriter wraps http.ResponseWriter to capture status code and response size.
 type responseWriter struct {
 	http.ResponseWriter
-	statusCode int
+	statusCode   int
+	bytesWritten int64
 }
 
 func newResponseWriter(w http.ResponseWriter) *responseWriter {
-	return &responseWriter{w, http.StatusOK}
+	return &responseWriter{ResponseWriter: w, statusCode: http.StatusOK}
 }
 
 func (rw *responseWriter) WriteHeader(code int) {
@@ -21,6 +24,12 @@ func (rw *responseWriter) WriteHeader(code int) {
 	rw.ResponseWriter.WriteHeader(code)
 }
 
+func (rw *responseWriter) Write(b []byte) (int, error) {
+	n, err := rw.ResponseWriter.Write(b)
+	rw.bytesWritten += int64(n)
+	return n, err
+}
+
 // Logger logs HTTP requests
 func Logger(next http.Handler) http.Handler {
 	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
@@ -29,14 +38,21 @@ func Logger(next http.Handler) http.Handler {
 		wrapped := newResponseWriter(w)
 		next.ServeHTTP(wrapped, r)
 
+		sc := trace.SpanContextFromContext(r.Context())
+		tid := ""
+		if sc.HasTraceID() {
+			tid = sc.TraceID().String()
+		}
+
 		duration := time.Since(start)
 
 		log.Printf(
-			"%s %s %d %s",
+			"%s %s %d %s trace_id=%s",
 			r.Method,
-			r.RequestURI,
+			r.URL.Path,
 			wrapped.statusCode,
 			duration,
+			tid,
 		)
 	})
 }

api/middleware/metrics.go

@@ -0,0 +1,215 @@
+package middleware
+
+import (
+	"net/http"
+	"strconv"
+	"time"
+
+	"github.com/go-chi/chi/v5"
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/promauto"
+	"github.com/prometheus/client_golang/prometheus/promhttp"
+)
+
+var (
+	httpRequestsTotal = promauto.NewCounterVec(
+		prometheus.CounterOpts{
+			Name: "http_requests_total",
+			Help: "Total HTTP requests processed, labeled by method, route, and status",
+		},
+		[]string{"method", "route", "status"},
+	)
+
+	httpRequestDuration = promauto.NewHistogramVec(
+		prometheus.HistogramOpts{
+			Name:    "http_request_duration_seconds",
+			Help:    "HTTP request latency in seconds, labeled by method and route",
+			Buckets: []float64{.0001, .0005, .001, .0025, .005, .01, .025, .05, .1, .25, .5, 1, 2.5, 5},
+		},
+		[]string{"method", "route"},
+	)
+
+	httpInflightRequests = promauto.NewGauge(
+		prometheus.GaugeOpts{
+			Name: "http_inflight_requests",
+			Help: "Number of HTTP requests currently being handled",
+		},
+	)
+
+	httpRequestSize = promauto.NewHistogramVec(
+		prometheus.HistogramOpts{
+			Name:    "http_request_size_bytes",
+			Help:    "HTTP request body size in bytes",
+			Buckets: prometheus.ExponentialBuckets(64, 4, 8),
+		},
+		[]string{"method", "route"},
+	)
+
+	httpResponseSize = promauto.NewHistogramVec(
+		prometheus.HistogramOpts{
+			Name:    "http_response_size_bytes",
+			Help:    "HTTP response body size in bytes",
+			Buckets: prometheus.ExponentialBuckets(64, 4, 8),
+		},
+		[]string{"method", "route"},
+	)
+
+	ordersCreatedTotal = promauto.NewCounterVec(
+		prometheus.CounterOpts{
+			Name: "orders_created_total",
+			Help: "Total orders successfully created, labeled by status",
+		},
+		[]string{"status"},
+	)
+
+	cartConversionTotal = promauto.NewCounterVec(
+		prometheus.CounterOpts{
+			Name: "cart_conversion_total",
+			Help: "Cart checkout outcomes (success, validation_failed, card_declined, stripe_failed, db_failed, payment_critical)",
+		},
+		[]string{"outcome"},
+	)
+
+	abandoned3DSSweepTotal = promauto.NewCounterVec(
+		prometheus.CounterOpts{
+			Name: "abandoned_3ds_sweep_total",
+			Help: "ReconcileStale3DSOrders outcomes per row processed (flipped, flip_noop, flip_failed, succeeded_skip, processing_skip, stripe_error, missing_pi, unrecognized_status)",
+		},
+		[]string{"outcome"},
+	)
+
+	orderValueDollars = promauto.NewHistogram(
+		prometheus.HistogramOpts{
+			Name:    "order_value_dollars",
+			Help:    "Distribution of completed order totals, in dollars",
+			Buckets: []float64{1, 5, 10, 20, 30, 50, 75, 100, 150, 250, 500, 1000},
+		},
+	)
+
+	stripeRequestDuration = promauto.NewHistogramVec(
+		prometheus.HistogramOpts{
+			Name:    "stripe_request_duration_seconds",
+			Help:    "Latency of outbound Stripe API calls",
+			Buckets: prometheus.DefBuckets,
+		},
+		[]string{"op", "outcome"},
+	)
+
+	authAttemptsTotal = promauto.NewCounterVec(
+		prometheus.CounterOpts{
+			Name: "auth_attempts_total",
+			Help: "Authentication attempts, by result (success, invalid_secret, missing_fingerprint, user_not_found, registered, error)",
+		},
+		[]string{"result"},
+	)
+
+	rateLimitRejectionsTotal = promauto.NewCounterVec(
+		prometheus.CounterOpts{
+			Name: "rate_limit_rejections_total",
+			Help: "Number of requests rejected by rate limiters",
+		},
+		[]string{"scope"},
+	)
+
+	logMessagesTotal = promauto.NewCounterVec(
+		prometheus.CounterOpts{
+			Name: "log_messages_total",
+			Help: "Total log lines emitted, labeled by level",
+		},
+		[]string{"level"},
+	)
+
+	buildInfo = promauto.NewGaugeVec(
+		prometheus.GaugeOpts{
+			Name: "terminalshop_build_info",
+			Help: "Build metadata; value is always 1, version is on the label",
+		},
+		[]string{"version"},
+	)
+)
+
+// Metrics records request count, latency, sizes, and concurrency for every request.
+func Metrics(next http.Handler) http.Handler {
+	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		start := time.Now()
+		wrapped := newResponseWriter(w)
+
+		httpInflightRequests.Inc()
+		defer httpInflightRequests.Dec()
+
+		next.ServeHTTP(wrapped, r)
+
+		route := chi.RouteContext(r.Context()).RoutePattern()
+		if route == "" {
+			route = "unknown"
+		}
+
+		duration := time.Since(start).Seconds()
+		status := strconv.Itoa(wrapped.statusCode)
+
+		httpRequestsTotal.WithLabelValues(r.Method, route, status).Inc()
+		httpRequestDuration.WithLabelValues(r.Method, route).Observe(duration)
+		if r.ContentLength > 0 {
+			httpRequestSize.WithLabelValues(r.Method, route).Observe(float64(r.ContentLength))
+		}
+		httpResponseSize.WithLabelValues(r.Method, route).Observe(float64(wrapped.bytesWritten))
+	})
+}
+
+// MetricsHandler returns the Prometheus scrape endpoint.
+func MetricsHandler() http.Handler {
+	return promhttp.Handler()
+}
+
+// SetBuildInfo records build metadata as a gauge of value 1.
+func SetBuildInfo(version string) {
+	buildInfo.WithLabelValues(version).Set(1)
+}
+
+// RecordOrderCreated records a successfully created order.
+func RecordOrderCreated(status string) {
+	ordersCreatedTotal.WithLabelValues(status).Inc()
+}
+
+// RecordCartConversion records the outcome of a checkout attempt.
+func RecordCartConversion(outcome string) {
+	cartConversionTotal.WithLabelValues(outcome).Inc()
+}
+
+// ObserveOrderValueCents records the value of a completed order (cents → dollars).
+func ObserveOrderValueCents(cents int) {
+	orderValueDollars.Observe(float64(cents) / 100.0)
+}
+
+// RecordAbandoned3DSSweep records the outcome of one row processed by
+// ReconcileStale3DSOrders. Bounded enumeration documented on the counter's
+// Help string.
+func RecordAbandoned3DSSweep(outcome string) {
+	abandoned3DSSweepTotal.WithLabelValues(outcome).Inc()
+}
+
+// Abandoned3DSSweepCounter exposes the sweep counter so tests can snapshot
+// per-label values via prometheus testutil. Not used in production code.
+func Abandoned3DSSweepCounter() *prometheus.CounterVec {
+	return abandoned3DSSweepTotal
+}
+
+// ObserveStripeRequest records latency of a Stripe API call.
+func ObserveStripeRequest(op, outcome string, durSec float64) {
+	stripeRequestDuration.WithLabelValues(op, outcome).Observe(durSec)
+}
+
+// RecordAuthAttempt records an authentication attempt outcome.
+func RecordAuthAttempt(result string) {
+	authAttemptsTotal.WithLabelValues(result).Inc()
+}
+
+// RecordRateLimitRejection records a request blocked by a rate limiter.
+func RecordRateLimitRejection(scope string) {
+	rateLimitRejectionsTotal.WithLabelValues(scope).Inc()
+}
+
+// RecordLogLevel increments the per-level log counter.
+func RecordLogLevel(level string) {
+	logMessagesTotal.WithLabelValues(level).Inc()
+}

api/middleware/ratelimit.go

@@ -4,6 +4,8 @@ import (
 	"net/http"
 	"time"
 
+	"strconv"
+
 	"github.com/go-chi/httprate"
 	"terminalShop/pkg/utils"
 )
@@ -14,6 +16,7 @@ func RateLimitByIP(limit int, window time.Duration) func(http.Handler) http.Hand
 		limit, window,
 		httprate.WithKeyFuncs(httprate.KeyByIP),
 		httprate.WithLimitHandler(func(w http.ResponseWriter, r *http.Request) {
+			RecordRateLimitRejection("ip")
 			utils.RespondError(w, http.StatusTooManyRequests, "RATE_LIMITED", "too many requests", nil)
 		}),
 	)
@@ -29,9 +32,10 @@ func RateLimitByUser(limit int, window time.Duration) func(http.Handler) http.Ha
 				// Fall back to IP if no user context (shouldn't happen on protected routes).
 				return httprate.KeyByIP(r)
 			}
-			return http.CanonicalHeaderKey("user") + ":" + string(rune(userID)), nil
+			return "user:" + strconv.FormatUint(uint64(userID), 10), nil
 		}),
 		httprate.WithLimitHandler(func(w http.ResponseWriter, r *http.Request) {
+			RecordRateLimitRejection("user")
 			utils.RespondError(w, http.StatusTooManyRequests, "RATE_LIMITED", "too many requests", nil)
 		}),
 	)

api/middleware/recovery.go

@@ -1,7 +1,7 @@
 package middleware
 
 import (
-	"log"
+	"log/slog"
 	"net/http"
 	"runtime/debug"
 
@@ -13,7 +13,12 @@ func Recovery(next http.Handler) http.Handler {
 	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		defer func() {
 			if err := recover(); err != nil {
-				log.Printf("PANIC: %v\n%s", err, debug.Stack())
+				slog.Error("panic recovered",
+					"error", err,
+					"method", r.Method,
+					"path", r.URL.Path,
+					"stack", string(debug.Stack()),
+				)
 
 				utils.RespondError(
 					w,

api/routes/doc.go

@@ -0,0 +1,3 @@
+// Package routes is the switchboard: it maps every URL to the handler that
+// knows what to do with it.
+package routes

api/routes/routes.go

@@ -9,26 +9,35 @@ import (
 	"terminalShop/api/handlers"
 	"terminalShop/api/middleware"
 	"terminalShop/pkg/auth"
+
+	"github.com/riandyrn/otelchi"
 )
 
 // SetupRoutes configures all API routes
 func SetupRoutes(
 	version string,
-	stripeSecretKey string,
 	stripeWebhookSecret string,
 	jwtManager *auth.JWTManager,
 	authFingerprintKey string,
 	shippoAPIKey string,
 	bringAPIUID string,
 	bringAPIKey string,
+	bringCustomerNumber string,
+	shippoWebhookSecret string,
 	appURL string,
+	slackSigningSecret string,
+	adminAPIKey string,
+	apiPort string,
+	maxOrderCents int,
 ) *chi.Mux {
 	r := chi.NewRouter()
 
 	// Global middleware
+	r.Use(otelchi.Middleware("terminalshop-api", otelchi.WithChiRoutes(r)))
 	r.Use(middleware.Logger)
 	r.Use(middleware.CORS())
 	r.Use(middleware.Recovery)
+	r.Use(middleware.Metrics)
 	r.Use(middleware.Auth(jwtManager))
 	// Broad IP-level rate limit: 200 req/min per IP across all endpoints.
 	r.Use(middleware.RateLimitByIP(200, time.Minute))
@@ -37,30 +46,45 @@ func SetupRoutes(
 	healthHandler := handlers.NewHealthHandler(version)
 	productHandler := handlers.NewProductHandler()
 	authHandler := handlers.NewAuthHandler(jwtManager, authFingerprintKey)
-	cartHandler := handlers.NewCartHandler(stripeSecretKey)
-	cardHandler := handlers.NewCardHandler(stripeSecretKey, appURL)
-	orderHandler := handlers.NewOrderHandler(stripeSecretKey)
+	cartHandler := handlers.NewCartHandler(appURL, maxOrderCents)
+	cardHandler := handlers.NewCardHandler(appURL)
+	orderHandler := handlers.NewOrderHandler(bringAPIUID, bringAPIKey, bringCustomerNumber)
 	addressHandler := handlers.NewAddressHandler(shippoAPIKey, bringAPIUID, bringAPIKey)
 	viewHandler := handlers.NewViewHandler()
-	webhookHandler := handlers.NewWebhookHandler(stripeWebhookSecret, stripeSecretKey)
-	sshKeyHandler := handlers.NewSSHKeyHandler()
+	webhookHandler := handlers.NewWebhookHandler(stripeWebhookSecret, shippoWebhookSecret)
+	slackHandler := handlers.NewSlackHandler(slackSigningSecret, adminAPIKey, apiPort, shippoWebhookSecret)
 
 	// Short payment redirect and success page — no auth required.
 	r.Get("/pay/{token}", handlers.PayRedirect)
+	r.Get("/t/{id}", handlers.TrackingRedirect)
 	r.Get("/card-added", func(w http.ResponseWriter, r *http.Request) {
 		w.Header().Set("Content-Type", "text/html")
-		w.Write([]byte(`<!DOCTYPE html><html><body style="font-family:monospace;text-align:center;padding:4rem"><h2>Card added.</h2><p>You can close this tab.</p></body></html>`))
+		_, _ = w.Write([]byte(`<!DOCTYPE html><html><body style="font-family:monospace;text-align:center;padding:4rem"><h2>Card added.</h2><p>You can close this tab.</p></body></html>`))
 	})
+	r.Get("/post-3ds", func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "text/html")
+		_, _ = w.Write([]byte(`<!DOCTYPE html><html><body style="font-family:monospace;text-align:center;padding:4rem"><h2>Authentication complete.</h2><p>Return to your terminal.</p></body></html>`))
+	})
+	r.Handle("/metrics", middleware.MetricsHandler())
 
 	r.Route("/api/v1", func(r chi.Router) {
-		// Health
+		// Health — accept HEAD for cheap probes from monitoring tools.
 		r.Get("/health", healthHandler.GetHealth)
+		r.Head("/health", healthHandler.GetHealth)
 		r.Get("/ping", healthHandler.Ping)
+		r.Head("/ping", healthHandler.Ping)
 
 		// Stripe webhooks — unauthenticated, verified via HMAC signature.
 		// Apply a generous IP rate limit here (Stripe retries from many IPs).
 		r.With(middleware.RateLimitByIP(60, time.Minute)).
 			Post("/webhooks/stripe", webhookHandler.HandleStripe)
+		r.With(middleware.RateLimitByIP(60, time.Minute)).
+			Post("/webhooks/shippo", webhookHandler.HandleShippo)
+
+		// Slack interactivity — unauthenticated at the HTTP layer; security
+		// comes from HMAC signature verification inside the handler.
+		r.With(middleware.RateLimitByIP(60, time.Minute)).
+			Post("/slack/interactivity", slackHandler.HandleInteractivity)
 
 		// Auth — stricter IP rate limit to protect against brute-force.
 		r.Group(func(r chi.Router) {
@@ -106,6 +130,9 @@ func SetupRoutes(
 
 			// Orders
 			r.Get("/orders", orderHandler.GetOrders)
+			r.Get("/orders/{id}/status", orderHandler.GetOrderStatus)
+			r.With(middleware.RateLimitByUser(10, time.Minute)).Post("/orders/{id}/retry-auth", cartHandler.RetryAuth)
+			r.Post("/orders/{id}/refund-request", orderHandler.CreateRefundRequest)
 			r.Post("/orders/{id}/refund", orderHandler.RefundOrder)
 
 			// Addresses
@@ -115,14 +142,13 @@ func SetupRoutes(
 				r.Delete("/{id}", addressHandler.DeleteAddress)
 				r.Put("/{id}/default", addressHandler.SetDefaultAddress)
 			})
+		})
 
-			// SSH Keys
-			r.Route("/ssh-keys", func(r chi.Router) {
-				// GET doesnt need id because it gets every ssh key
-				r.Get("/", sshKeyHandler.GetSSHKeys)
-				// Delete needs an id to delete only one key
-				r.Delete("/{id}", sshKeyHandler.DeleteSSHKeys)
-			})
+		// Admin endpoints, gated by ADMIN_API_KEY only, no JWT required
+		r.Group(func(r chi.Router) {
+			r.Use(middleware.RequireAdmin)
+			r.Patch("/orders/{id}/tracking", orderHandler.UpdateTracking)
+			r.Post("/orders/{id}/label", orderHandler.PurchaseLabel)
 		})
 	})
 

cmd/reconcile-cards/doc.go

@@ -0,0 +1,3 @@
+// Command reconcile-cards hunts down saved cards that Stripe no longer knows
+// about and detaches them. Run it with -dry-run first if you're nervous.
+package main

cmd/reconcile-cards/main.go

@@ -0,0 +1,73 @@
+package main
+
+import (
+	"flag"
+	"log"
+	"terminalShop/pkg/config"
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+
+	"github.com/stripe/stripe-go/v78"
+	"github.com/stripe/stripe-go/v78/paymentmethod"
+)
+
+func main() {
+	dryRun := flag.Bool("dry-run", false, "list orphans without detaching")
+	flag.Parse()
+
+	cfg, err := config.Load()
+	if err != nil {
+		log.Fatalf("config: %v", err)
+	}
+	if _, err := database.Connect(cfg.DatabaseURL); err != nil {
+		log.Fatalf("db: %v", err)
+	}
+	db := database.GetDB()
+	stripe.Key = cfg.StripeSecretKey
+
+	var users []models.User
+	if err := db.Where("stripe_customer_id != ''").Find(&users).Error; err != nil {
+		log.Fatalf("list users: %v", err)
+	}
+
+	totalOrphans, totalDetached := 0, 0
+	for _, user := range users {
+		var activeCards []models.Card
+		if err := db.Where("user_id = ?", user.ID).Find(&activeCards).Error; err != nil {
+			log.Printf("user %d: list cards: %v", user.ID, err)
+			continue
+		}
+		keep := make(map[string]bool, len(activeCards))
+		for _, card := range activeCards {
+			keep[card.StripePaymentID] = true
+		}
+		iter := paymentmethod.List(&stripe.PaymentMethodListParams{
+			Customer: stripe.String(user.StripeCustomerID),
+			Type:     stripe.String("card"),
+		})
+		for iter.Next() {
+			pm := iter.PaymentMethod()
+			if keep[pm.ID] {
+				continue
+			}
+			totalOrphans++
+			last4 := ""
+			if pm.Card != nil {
+				last4 = pm.Card.Last4
+			}
+			log.Printf("orphan: user=%d cus=%s pm=%s last4=%s", user.ID, user.StripeCustomerID, pm.ID, last4)
+			if *dryRun {
+				continue
+			}
+			if _, err := paymentmethod.Detach(pm.ID, nil); err != nil {
+				log.Printf("  detach failed: %v", err)
+				continue
+			}
+			totalDetached++
+		}
+		if err := iter.Err(); err != nil {
+			log.Printf("user %d: list pms: %v", user.ID, err)
+		}
+	}
+	log.Printf("done. orphans=%d detached=%d dry_run=%v", totalOrphans, totalDetached, *dryRun)
+}

cog.toml

@@ -0,0 +1,25 @@
+from_latest_tag = false
+ignore_merge_commits = false
+ignore_fixup_commits = false
+disable_changelog = false
+disable_bump_commit = false
+generate_mono_repository_global_tag = true
+generate_mono_repository_package_tags = true
+branch_whitelist = []
+pre = "alpha.*"
+skip_ci = "[skip ci]"
+skip_untracked = false
+pre_bump_hooks = []
+post_bump_hooks = []
+pre_package_bump_hooks = []
+post_package_bump_hooks = []
+
+[git_hooks]
+
+[commit_types]
+
+[changelog]
+path = "CHANGELOG.md"
+authors = []
+
+[bump_profiles]

go.mod

@@ -1,73 +1,130 @@
 module terminalShop
 
-go 1.25.7
+go 1.25.9
 
 require (
-	github.com/charmbracelet/bubbletea v1.3.10
-	github.com/charmbracelet/huh v0.8.0
-	github.com/charmbracelet/lipgloss v1.1.0
+	charm.land/bubbles/v2 v2.1.0
+	charm.land/bubbletea/v2 v2.0.6
+	charm.land/huh/v2 v2.0.3
+	charm.land/lipgloss/v2 v2.0.3
+	charm.land/wish/v2 v2.0.1
 	github.com/charmbracelet/ssh v0.0.0-20250826160808-ebfa259c7309
-	github.com/charmbracelet/wish v1.4.7
+	github.com/foize/go.sgr v0.0.0-20140220094842-40bdfc98040c
 	github.com/go-chi/chi/v5 v5.2.5
 	github.com/go-chi/cors v1.2.2
+	github.com/go-chi/httprate v0.15.0
 	github.com/golang-jwt/jwt/v5 v5.3.1
 	github.com/joho/godotenv v1.5.1
-	golang.org/x/crypto v0.48.0
+	github.com/prometheus/client_golang v1.23.2
+	github.com/riandyrn/otelchi v0.12.2
+	github.com/stripe/stripe-go/v78 v78.12.0
+	go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp v0.68.0
+	go.opentelemetry.io/otel v1.43.0
+	go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracehttp v1.43.0
+	go.opentelemetry.io/otel/sdk v1.43.0
+	go.opentelemetry.io/otel/trace v1.43.0
+	golang.org/x/crypto v0.50.0
+	gorm.io/driver/postgres v1.6.0
 	gorm.io/driver/sqlite v1.6.0
 	gorm.io/gorm v1.31.1
+	gorm.io/plugin/opentelemetry v0.1.16
+	rsc.io/qr v0.2.0
 )
 
 require (
+	charm.land/log/v2 v2.0.0 // indirect
+	github.com/ClickHouse/ch-go v0.61.5 // indirect
+	github.com/ClickHouse/clickhouse-go/v2 v2.30.0 // indirect
+	github.com/andybalholm/brotli v1.1.1 // indirect
 	github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be // indirect
 	github.com/atotto/clipboard v0.1.4 // indirect
-	github.com/aymanbagabas/go-osc52/v2 v2.0.1 // indirect
+	github.com/beorn7/perks v1.0.1 // indirect
+	github.com/bitfield/gotestdox v0.2.2 // indirect
 	github.com/catppuccin/go v0.3.0 // indirect
-	github.com/charmbracelet/bubbles v0.21.1-0.20250623103423-23b8fd6302d7 // indirect
-	github.com/charmbracelet/colorprofile v0.4.1 // indirect
-	github.com/charmbracelet/keygen v0.5.3 // indirect
-	github.com/charmbracelet/log v0.4.1 // indirect
-	github.com/charmbracelet/x/ansi v0.11.6 // indirect
-	github.com/charmbracelet/x/cellbuf v0.0.15 // indirect
-	github.com/charmbracelet/x/conpty v0.1.0 // indirect
-	github.com/charmbracelet/x/errors v0.0.0-20240508181413-e8d8b6e2de86 // indirect
+	github.com/cenkalti/backoff/v5 v5.0.3 // indirect
+	github.com/cespare/xxhash/v2 v2.3.0 // indirect
+	github.com/charmbracelet/colorprofile v0.4.3 // indirect
+	github.com/charmbracelet/keygen v0.5.4 // indirect
+	github.com/charmbracelet/ultraviolet v0.0.0-20260416155717-489999b90468 // indirect
+	github.com/charmbracelet/x/ansi v0.11.7 // indirect
+	github.com/charmbracelet/x/conpty v0.1.1 // indirect
+	github.com/charmbracelet/x/errors v0.0.0-20251110184232-6ab307057ac7 // indirect
+	github.com/charmbracelet/x/exp/ordered v0.1.0 // indirect
 	github.com/charmbracelet/x/exp/strings v0.0.0-20240722160745-212f7b056ed0 // indirect
-	github.com/charmbracelet/x/input v0.3.4 // indirect
 	github.com/charmbracelet/x/term v0.2.2 // indirect
 	github.com/charmbracelet/x/termios v0.1.1 // indirect
-	github.com/charmbracelet/x/windows v0.2.0 // indirect
-	github.com/clipperhouse/displaywidth v0.9.0 // indirect
-	github.com/clipperhouse/stringish v0.1.1 // indirect
-	github.com/clipperhouse/uax29/v2 v2.5.0 // indirect
+	github.com/charmbracelet/x/windows v0.2.2 // indirect
+	github.com/clipperhouse/displaywidth v0.11.0 // indirect
+	github.com/clipperhouse/uax29/v2 v2.7.0 // indirect
 	github.com/creack/pty v1.1.24 // indirect
+	github.com/dnephin/pflag v1.0.7 // indirect
 	github.com/dustin/go-humanize v1.0.1 // indirect
-	github.com/erikgeiser/coninput v0.0.0-20211004153227-1c3628e74d0f // indirect
-	github.com/foize/go.sgr v0.0.0-20140220094842-40bdfc98040c // indirect
-	github.com/go-chi/httprate v0.15.0 // indirect
-	github.com/go-logfmt/logfmt v0.6.0 // indirect
+	github.com/fatih/color v1.18.0 // indirect
+	github.com/felixge/httpsnoop v1.0.4 // indirect
+	github.com/fsnotify/fsnotify v1.9.0 // indirect
+	github.com/go-faster/city v1.0.1 // indirect
+	github.com/go-faster/errors v0.7.1 // indirect
+	github.com/go-logfmt/logfmt v0.6.1 // indirect
+	github.com/go-logr/logr v1.4.3 // indirect
+	github.com/go-logr/stdr v1.2.2 // indirect
+	github.com/go-sql-driver/mysql v1.7.0 // indirect
+	github.com/google/shlex v0.0.0-20191202100458-e7afc7fbc510 // indirect
+	github.com/google/uuid v1.6.0 // indirect
+	github.com/gotesttools/gotestfmt/v2 v2.5.0 // indirect
+	github.com/grpc-ecosystem/grpc-gateway/v2 v2.28.0 // indirect
+	github.com/hashicorp/go-version v1.6.0 // indirect
 	github.com/jackc/pgpassfile v1.0.0 // indirect
 	github.com/jackc/pgservicefile v0.0.0-20240606120523-5a60cdf6a761 // indirect
 	github.com/jackc/pgx/v5 v5.6.0 // indirect
 	github.com/jackc/puddle/v2 v2.2.2 // indirect
 	github.com/jinzhu/inflection v1.0.0 // indirect
 	github.com/jinzhu/now v1.1.5 // indirect
+	github.com/klauspost/compress v1.18.0 // indirect
 	github.com/klauspost/cpuid/v2 v2.2.10 // indirect
-	github.com/lucasb-eyer/go-colorful v1.3.0 // indirect
+	github.com/kylelemons/godebug v1.1.0 // indirect
+	github.com/lucasb-eyer/go-colorful v1.4.0 // indirect
+	github.com/mattn/go-colorable v0.1.13 // indirect
 	github.com/mattn/go-isatty v0.0.20 // indirect
-	github.com/mattn/go-localereader v0.0.1 // indirect
-	github.com/mattn/go-runewidth v0.0.19 // indirect
+	github.com/mattn/go-runewidth v0.0.23 // indirect
 	github.com/mattn/go-sqlite3 v1.14.34 // indirect
 	github.com/mitchellh/hashstructure/v2 v2.0.2 // indirect
-	github.com/muesli/ansi v0.0.0-20230316100256-276c6243b2f6 // indirect
 	github.com/muesli/cancelreader v0.2.2 // indirect
-	github.com/muesli/termenv v0.16.0 // indirect
+	github.com/munnerz/goautoneg v0.0.0-20191010083416-a7dc8b61c822 // indirect
+	github.com/paulmach/orb v0.11.1 // indirect
+	github.com/pierrec/lz4/v4 v4.1.21 // indirect
+	github.com/pkg/errors v0.9.1 // indirect
+	github.com/prometheus/client_model v0.6.2 // indirect
+	github.com/prometheus/common v0.66.1 // indirect
+	github.com/prometheus/procfs v0.16.1 // indirect
 	github.com/rivo/uniseg v0.4.7 // indirect
-	github.com/stripe/stripe-go/v78 v78.12.0 // indirect
+	github.com/segmentio/asm v1.2.0 // indirect
+	github.com/shopspring/decimal v1.4.0 // indirect
 	github.com/xo/terminfo v0.0.0-20220910002029-abceb7e1c41e // indirect
 	github.com/zeebo/xxh3 v1.0.2 // indirect
-	golang.org/x/exp v0.0.0-20240719175910-8a7402abbf56 // indirect
-	golang.org/x/sync v0.19.0 // indirect
-	golang.org/x/sys v0.41.0 // indirect
-	golang.org/x/text v0.34.0 // indirect
-	gorm.io/driver/postgres v1.6.0 // indirect
-	rsc.io/qr v0.2.0 // indirect
+	go.opentelemetry.io/auto/sdk v1.2.1 // indirect
+	go.opentelemetry.io/otel/exporters/otlp/otlptrace v1.43.0 // indirect
+	go.opentelemetry.io/otel/metric v1.43.0 // indirect
+	go.opentelemetry.io/proto/otlp v1.10.0 // indirect
+	go.yaml.in/yaml/v2 v2.4.2 // indirect
+	golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546 // indirect
+	golang.org/x/mod v0.34.0 // indirect
+	golang.org/x/net v0.52.0 // indirect
+	golang.org/x/sync v0.20.0 // indirect
+	golang.org/x/sys v0.43.0 // indirect
+	golang.org/x/term v0.42.0 // indirect
+	golang.org/x/text v0.36.0 // indirect
+	golang.org/x/tools v0.43.0 // indirect
+	google.golang.org/genproto/googleapis/api v0.0.0-20260401024825-9d38bb4040a9 // indirect
+	google.golang.org/genproto/googleapis/rpc v0.0.0-20260401024825-9d38bb4040a9 // indirect
+	google.golang.org/grpc v1.80.0 // indirect
+	google.golang.org/protobuf v1.36.11 // indirect
+	gopkg.in/yaml.v3 v3.0.1 // indirect
+	gorm.io/driver/clickhouse v0.7.0 // indirect
+	gorm.io/driver/mysql v1.5.7 // indirect
+	gotest.tools/gotestsum v1.13.0 // indirect
+)
+
+tool (
+	github.com/gotesttools/gotestfmt/v2/cmd/gotestfmt
+	gotest.tools/gotestsum
 )

go.sum

@@ -1,82 +1,128 @@
+charm.land/bubbles/v2 v2.1.0 h1:YSnNh5cPYlYjPxRrzs5VEn3vwhtEn3jVGRBT3M7/I0g=
+charm.land/bubbles/v2 v2.1.0/go.mod h1:l97h4hym2hvWBVfmJDtrEHHCtkIKeTEb3TTJ4ZOB3wY=
+charm.land/bubbletea/v2 v2.0.6 h1:UHN/91OyuhaOFGSrBXQ/hMZD8IO1Uc4BvHlgHXL2WJo=
+charm.land/bubbletea/v2 v2.0.6/go.mod h1:MH/D8ZLlN3op37vQvijKuU29g3rqTp+aQapURFonF9g=
+charm.land/huh/v2 v2.0.3 h1:2cJsMqEPwSywGHvdlKsJyQKPtSJLVnFKyFbsYZTlLkU=
+charm.land/huh/v2 v2.0.3/go.mod h1:93eEveeeqn47MwiC3tf+2atZ2l7Is88rAtmZNZ8x9Wc=
+charm.land/lipgloss/v2 v2.0.3 h1:yM2zJ4Cf5Y51b7RHIwioil4ApI/aypFXXVHSwlM6RzU=
+charm.land/lipgloss/v2 v2.0.3/go.mod h1:7myLU9iG/3xluAWzpY/fSxYYHCgoKTie7laxk6ATwXA=
+charm.land/log/v2 v2.0.0 h1:SY3Cey7ipx86/MBXQHwsguOT6X1exT94mmJRdzTNs+s=
+charm.land/log/v2 v2.0.0/go.mod h1:c3cZSRqm20qUVVAR1WmS/7ab8bgha3C6G7DjPcaVZz0=
+charm.land/wish/v2 v2.0.1 h1:xYOsvQG/bYNRoKUBt0AEyMiCv9rksmCOG/fD5WifAzg=
+charm.land/wish/v2 v2.0.1/go.mod h1:uBWdsKTFk9BE0JsdEv8KKF8/abBfRe/hKEGOBm3OKZA=
+github.com/ClickHouse/ch-go v0.61.5 h1:zwR8QbYI0tsMiEcze/uIMK+Tz1D3XZXLdNrlaOpeEI4=
+github.com/ClickHouse/ch-go v0.61.5/go.mod h1:s1LJW/F/LcFs5HJnuogFMta50kKDO0lf9zzfrbl0RQg=
+github.com/ClickHouse/clickhouse-go/v2 v2.30.0 h1:AG4D/hW39qa58+JHQIFOSnxyL46H6h2lrmGGk17dhFo=
+github.com/ClickHouse/clickhouse-go/v2 v2.30.0/go.mod h1:i9ZQAojcayW3RsdCb3YR+n+wC2h65eJsZCscZ1Z1wyo=
 github.com/MakeNowJust/heredoc v1.0.0 h1:cXCdzVdstXyiTqTvfqk9SDHpKNjxuom+DOlyEeQ4pzQ=
 github.com/MakeNowJust/heredoc v1.0.0/go.mod h1:mG5amYoWBHf8vpLOuehzbGGw0EHxpZZ6lCpQ4fNJ8LE=
+github.com/andybalholm/brotli v1.1.1 h1:PR2pgnyFznKEugtsUo0xLdDop5SKXd5Qf5ysW+7XdTA=
+github.com/andybalholm/brotli v1.1.1/go.mod h1:05ib4cKhjx3OQYUY22hTVd34Bc8upXjOLL2rKwwZBoA=
 github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be h1:9AeTilPcZAjCFIImctFaOjnTIavg87rW78vTPkQqLI8=
 github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be/go.mod h1:ySMOLuWl6zY27l47sB3qLNK6tF2fkHG55UZxx8oIVo4=
 github.com/atotto/clipboard v0.1.4 h1:EH0zSVneZPSuFR11BlR9YppQTVDbh5+16AmcJi4g1z4=
 github.com/atotto/clipboard v0.1.4/go.mod h1:ZY9tmq7sm5xIbd9bOK4onWV4S6X0u6GY7Vn0Yu86PYI=
-github.com/aymanbagabas/go-osc52/v2 v2.0.1 h1:HwpRHbFMcZLEVr42D4p7XBqjyuxQH5SMiErDT4WkJ2k=
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loadtest/overnight.js

@@ -0,0 +1,186 @@
+import http from 'k6/http';
+
+const BASE = __ENV.BASE_URL || 'https://api.sshops.uk';
+const SECRET = __ENV.CLIENT_SECRET || '';
+
+// Per-VU JWT cache. JWTs are valid for 30 minutes; we refresh ~5 min early.
+let cachedToken = null;
+let cachedExpiresAt = 0;
+let cachedFingerprint = null;
+
+// SSHPublicKey has a uniqueIndex constraint, so each VU needs a distinct
+// (fake but unique) public key string. Suffixing with VU+timestamp keeps
+// the full text unique without affecting the rest of the body.
+let cachedPubkey = null;
+
+function getToken() {
+  const now = Date.now();
+  if (cachedToken && now < cachedExpiresAt) return cachedToken;
+
+  if (!cachedFingerprint) {
+    cachedFingerprint = `SHA256:k6-${__VU}-${now.toString(36)}`;
+    cachedPubkey = `ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAILoadTest${__VU}-${now.toString(36)} k6@vu${__VU}`;
+  }
+
+  const res = http.post(
+    `${BASE}/api/v1/auth/token`,
+    JSON.stringify({
+      client_secret: SECRET,
+      fingerprint: cachedFingerprint,
+      ssh_public_key: cachedPubkey,
+    }),
+    { headers: { 'Content-Type': 'application/json' }, tags: { name: 'auth_token_refresh' } },
+  );
+
+  if (res.status !== 200) return null;
+  const body = JSON.parse(res.body);
+  cachedToken = body.access_token;
+  cachedExpiresAt = now + (body.expires_in - 300) * 1000;
+  return cachedToken;
+}
+
+function authHeaders() {
+  const tok = getToken();
+  return tok ? { Authorization: `Bearer ${tok}`, 'Content-Type': 'application/json' } : null;
+}
+
+// Rate limits we are operating under (per-IP, single source IP):
+//   global ........... 200 req/min
+//   /api/v1/auth/* ...  20 req/min  (auth/register, auth/user, auth/token)
+//   /api/v1/webhooks/   60 req/min
+// All rates below are tuned to stay UNDER these ceilings with headroom so
+// nothing gets rate-limited and the histogram captures real handler latency.
+// Total ~148 req/min combined. Wall time ~10h.
+export const options = {
+  discardResponseBodies: true,
+  summaryTrendStats: ['avg', 'p(95)', 'p(99)', 'max'],
+  scenarios: {
+    browse: {
+      // /products, /products/{id}, /health, /ping. Only the global 200/min
+      // limit applies to these. Hold steady at 100/min all night so we never
+      // get close to the ceiling no matter what other scenarios do.
+      executor: 'constant-arrival-rate',
+      rate: 100,
+      timeUnit: '1m',
+      duration: '10h',
+      preAllocatedVUs: 5,
+      maxVUs: 20,
+      exec: 'browse',
+    },
+    err_404: {
+      // /products/{99xxx} — chi route still matches, returns 404. Counts
+      // against the global 200/min only.
+      executor: 'constant-arrival-rate',
+      rate: 30,
+      timeUnit: '1m',
+      duration: '10h',
+      preAllocatedVUs: 3,
+      maxVUs: 10,
+      exec: 'notFound',
+    },
+    auth_lookup: {
+      // GET /auth/user — counts against the /auth/* 20/min group ceiling
+      // SHARED with auth_warn. We split: 10/min lookup + 8/min warn = 18/min.
+      executor: 'constant-arrival-rate',
+      rate: 10,
+      timeUnit: '1m',
+      duration: '10h',
+      preAllocatedVUs: 2,
+      maxVUs: 5,
+      exec: 'authLookup',
+    },
+    auth_warn: {
+      // POST /auth/token with bad creds — same 20/min group ceiling as above.
+      executor: 'constant-arrival-rate',
+      rate: 8,
+      timeUnit: '1m',
+      duration: '10h',
+      preAllocatedVUs: 2,
+      maxVUs: 5,
+      exec: 'authBad',
+    },
+  },
+};
+
+export default function () {
+  // Smoke-test entry point for `--vus N --duration T` runs.
+  browse();
+  authBad();
+  authLookup();
+  notFound();
+  if (SECRET) {
+    authedBrowse();
+    convertFail();
+    addressBad();
+  }
+}
+
+export function browse() {
+  const r = Math.random();
+  if (r < 0.6)       http.get(`${BASE}/api/v1/products`,   { tags: { name: 'list_products' } });
+  else if (r < 0.8)  http.get(`${BASE}/api/v1/products/1`, { tags: { name: 'get_product' } });
+  else if (r < 0.95) http.get(`${BASE}/api/v1/health`,     { tags: { name: 'health' } });
+  else               http.get(`${BASE}/api/v1/ping`,       { tags: { name: 'ping' } });
+}
+
+export function authedBrowse() {
+  const h = authHeaders();
+  if (!h) return;
+  const r = Math.random();
+  if (r < 0.4)       http.get(`${BASE}/api/v1/cart`,      { headers: h, tags: { name: 'authed_get_cart' } });
+  else if (r < 0.6)  http.get(`${BASE}/api/v1/cards`,     { headers: h, tags: { name: 'authed_list_cards' } });
+  else if (r < 0.8)  http.get(`${BASE}/api/v1/addresses`, { headers: h, tags: { name: 'authed_list_addresses' } });
+  else               http.get(`${BASE}/api/v1/orders`,    { headers: h, tags: { name: 'authed_list_orders' } });
+}
+
+export function convertFail() {
+  const h = authHeaders();
+  if (!h) return;
+  // Reset cart, drop one item in, attempt convert. No card/address selected
+  // → ConvertCart hits validation_missing_address → cart_conversion_total
+  // outcome=validation_missing_address + audit.OrderFailed warn.
+  http.del(`${BASE}/api/v1/cart`, null, { headers: h, tags: { name: 'cart_clear' } });
+  http.put(
+    `${BASE}/api/v1/cart/item`,
+    JSON.stringify({ coffee_id: 1, quantity: 1 }),
+    { headers: h, tags: { name: 'cart_add_item' } },
+  );
+  http.post(`${BASE}/api/v1/cart/convert`, null, { headers: h, tags: { name: 'cart_convert_fail' } });
+}
+
+export function addressBad() {
+  const h = authHeaders();
+  if (!h) return;
+  // Junk US zip + street → shippo validation fails → addressLog.Warn.
+  http.post(
+    `${BASE}/api/v1/addresses`,
+    JSON.stringify({
+      name: 'Load Test',
+      street: 'asdfasdfasdf',
+      city: 'Nowhere',
+      state: 'XX',
+      zip: '00000',
+      country: 'US',
+      phone: '+15555550000',
+    }),
+    { headers: h, tags: { name: 'address_create_bad' } },
+  );
+}
+
+export function authBad() {
+  http.post(
+    `${BASE}/api/v1/auth/token`,
+    JSON.stringify({ client_secret: 'definitely_wrong', fingerprint: 'SHA256:fake' }),
+    { headers: { 'Content-Type': 'application/json' }, tags: { name: 'auth_bad_creds' } },
+  );
+}
+
+export function authLookup() {
+  const fp = `SHA256:${Math.random().toString(36).slice(2, 14)}`;
+  http.get(`${BASE}/api/v1/auth/user?fingerprint=${fp}`, { tags: { name: 'auth_user_lookup' } });
+}
+
+export function notFound() {
+  const id = 99000 + Math.floor(Math.random() * 1000);
+  http.get(`${BASE}/api/v1/products/${id}`, { tags: { name: 'product_not_found' } });
+}

main.go

@@ -8,24 +8,20 @@ import (
 	"os"
 	"os/signal"
 	"syscall"
-
 	"time"
 
-	tea "github.com/charmbracelet/bubbletea"
+	tea "charm.land/bubbletea/v2"
+	"charm.land/wish/v2"
+	"charm.land/wish/v2/bubbletea"
+	"charm.land/wish/v2/logging"
 	"github.com/charmbracelet/ssh"
-	"github.com/charmbracelet/wish"
-	"github.com/charmbracelet/wish/bubbletea"
-	"github.com/charmbracelet/wish/logging"
+	"github.com/stripe/stripe-go/v78"
 
 	"terminalShop/pkg/auth"
 	"terminalShop/pkg/config"
 	"terminalShop/pkg/tui"
 )
 
-const (
-	port = "23456"
-)
-
 func listenHost() string {
 	if h := os.Getenv("SSH_HOST"); h != "" {
 		return h
@@ -33,23 +29,12 @@ func listenHost() string {
 	return "localhost"
 }
 
-func listenPort() string {
-	if p := os.Getenv("SSH_PORT"); p != "" {
-		return p
-	}
-	return port
-}
-
 var (
 	apiURL             string
 	authFingerprintKey string
-	stripePublicKey    string
 )
 
 func teaHandler(s ssh.Session) (tea.Model, []tea.ProgramOption) {
-	renderer := bubbletea.MakeRenderer(s)
-
-	// Extract SSH public key from session
 	pubKey := s.PublicKey()
 
 	var fingerprint, pubKeyStr string
@@ -58,9 +43,8 @@ func teaHandler(s ssh.Session) (tea.Model, []tea.ProgramOption) {
 		pubKeyStr = auth.FormatSSHPublicKey(pubKey)
 	}
 
-	// Create TUI model with user context (no registration screen needed!)
-	m := tui.NewModelWithAuth(renderer, fingerprint, pubKeyStr, apiURL, authFingerprintKey, stripePublicKey)
-	return m, []tea.ProgramOption{tea.WithAltScreen()}
+	m := tui.NewModelWithAuth(fingerprint, pubKeyStr, apiURL, authFingerprintKey)
+	return m, nil
 }
 
 func main() {
@@ -73,12 +57,20 @@ func main() {
 	// Set API URL and auth key from config for TUI connections
 	apiURL = cfg.APIURL
 	authFingerprintKey = cfg.AuthFingerprintKey
-	stripePublicKey = cfg.StripePublicKey
+
+	// Wire the publishable key into stripe-go's package-level global once.
+	// TUI uses the legacy Tokens API (stripetoken.New) which accepts the
+	// publishable key; per-session writes would race across concurrent SSH
+	// sessions even though they'd all write the same value.
+	// NOTE: assumes single-process — if you ever embed both the SSH and API
+	// binaries together, the last writer wins and one of them silently breaks.
+	stripe.Key = cfg.StripePublicKey
+
 	log.Printf("TUI will connect to API at: %s", apiURL)
 
 	// Create SSH server
 	host := listenHost()
-	p := listenPort()
+	p := cfg.SSHPort
 	s, err := wish.NewServer(
 		wish.WithAddress(fmt.Sprintf("%s:%s", host, p)),
 		wish.WithHostKeyPath(".ssh/term_info_ed25519"),

pkg/api/client.go

@@ -56,7 +56,6 @@ type TokenResponse struct {
 }
 
 func (c *Client) GetOrCreateToken(fingerprint, pubKeyStr, clientSecret string) (string, models.PublicUser, error) {
-
 	url := fmt.Sprintf("%s/api/v1/auth/token", c.BaseURL)
 
 	reqBody := TokenRequest{
@@ -80,7 +79,7 @@ func (c *Client) GetOrCreateToken(fingerprint, pubKeyStr, clientSecret string) (
 	if err != nil {
 		return "", models.PublicUser{}, fmt.Errorf("token refresh request failed: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	if resp.StatusCode != http.StatusOK {
 		return "", models.PublicUser{}, fmt.Errorf("token refresh returned status %d", resp.StatusCode)
@@ -105,16 +104,16 @@ func (c *Client) RefreshToken(fingerprint, clientSecret string) (string, error)
 
 // APIResponse represents the standard API response format
 type APIResponse struct {
-	Success bool                   `json:"success"`
-	Data    map[string]interface{} `json:"data"`
-	Error   *APIError              `json:"error,omitempty"`
+	Success bool           `json:"success"`
+	Data    map[string]any `json:"data"`
+	Error   *APIError      `json:"error,omitempty"`
 }
 
 // APIError represents an error from the API
 type APIError struct {
-	Code    string                 `json:"code"`
-	Message string                 `json:"message"`
-	Details map[string]interface{} `json:"details,omitempty"`
+	Code    string         `json:"code"`
+	Message string         `json:"message"`
+	Details map[string]any `json:"details,omitempty"`
 }
 
 // ProductsResponse represents the products API response
@@ -137,7 +136,7 @@ func (c *Client) GetProducts() ([]models.Coffee, error) {
 	if err != nil {
 		return nil, fmt.Errorf("failed to fetch products: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	if resp.StatusCode != http.StatusOK {
 		return nil, fmt.Errorf("API returned status %d", resp.StatusCode)
@@ -167,7 +166,7 @@ func (c *Client) Health() error {
 	if err != nil {
 		return fmt.Errorf("health check failed: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	if resp.StatusCode != http.StatusOK {
 		return fmt.Errorf("API returned status %d", resp.StatusCode)
@@ -217,7 +216,7 @@ func (c *Client) RegisterUser(username, sshPublicKey, sshKeyFingerprint string)
 	if err != nil {
 		return nil, fmt.Errorf("failed to register user: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var registerResp RegisterResponse
 	if err := json.NewDecoder(resp.Body).Decode(&registerResp); err != nil {
@@ -281,14 +280,31 @@ type CardResponse struct {
 }
 
 // ConvertCartResponse represents the cart conversion (checkout) API response.
+// 200 carries Order populated; 202 (requires_action / 3DS) carries the
+// redirect fields and OrderID instead.
 type ConvertCartResponse struct {
 	Success bool `json:"success"`
 	Data    struct {
-		Order models.Order `json:"order"`
+		Order           *models.Order `json:"order,omitempty"`
+		OrderID         uint          `json:"order_id,omitempty"`
+		PaymentIntentID string        `json:"payment_intent_id,omitempty"`
+		Status          string        `json:"status,omitempty"`
+		RedirectToken   string        `json:"redirect_token,omitempty"`
+		RedirectURL     string        `json:"redirect_url,omitempty"`
 	} `json:"data"`
 	Error *APIError `json:"error,omitempty"`
 }
 
+// CheckoutOutcome is the unified result of ConvertCart. RequiresAction=true
+// means the customer needs to complete 3DS at RedirectURL; poll
+// GetOrderStatus(OrderID) until the webhook flips the order to paid or failed.
+type CheckoutOutcome struct {
+	Order          *models.Order
+	OrderID        uint
+	RequiresAction bool
+	RedirectURL    string
+}
+
 // GetCart fetches the user's current cart.
 func (c *Client) GetCart() (*CartData, error) {
 	url := fmt.Sprintf("%s/api/v1/cart", c.BaseURL)
@@ -302,7 +318,7 @@ func (c *Client) GetCart() (*CartData, error) {
 	if err != nil {
 		return nil, fmt.Errorf("failed to fetch cart: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var cartResp CartResponse
 	if err := json.NewDecoder(resp.Body).Decode(&cartResp); err != nil {
@@ -323,7 +339,7 @@ func (c *Client) GetCart() (*CartData, error) {
 func (c *Client) SetCartItem(coffeeID uint, quantity int) (*CartData, error) {
 	url := fmt.Sprintf("%s/api/v1/cart/item", c.BaseURL)
 
-	body := map[string]interface{}{
+	body := map[string]any{
 		"coffee_id": coffeeID,
 		"quantity":  quantity,
 	}
@@ -342,7 +358,7 @@ func (c *Client) SetCartItem(coffeeID uint, quantity int) (*CartData, error) {
 	if err != nil {
 		return nil, fmt.Errorf("failed to set cart item: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var cartResp CartResponse
 	if err := json.NewDecoder(resp.Body).Decode(&cartResp); err != nil {
@@ -363,7 +379,7 @@ func (c *Client) SetCartItem(coffeeID uint, quantity int) (*CartData, error) {
 func (c *Client) SetCartAddress(addressID uint) error {
 	url := fmt.Sprintf("%s/api/v1/cart/address", c.BaseURL)
 
-	body := map[string]interface{}{
+	body := map[string]any{
 		"address_id": addressID,
 	}
 	jsonData, err := json.Marshal(body)
@@ -381,7 +397,7 @@ func (c *Client) SetCartAddress(addressID uint) error {
 	if err != nil {
 		return fmt.Errorf("failed to set cart address: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var result APIResponse
 	if err := json.NewDecoder(resp.Body).Decode(&result); err != nil {
@@ -402,7 +418,7 @@ func (c *Client) SetCartAddress(addressID uint) error {
 func (c *Client) SetCartCard(cardID uint) error {
 	url := fmt.Sprintf("%s/api/v1/cart/card", c.BaseURL)
 
-	body := map[string]interface{}{
+	body := map[string]any{
 		"card_id": cardID,
 	}
 	jsonData, err := json.Marshal(body)
@@ -420,7 +436,7 @@ func (c *Client) SetCartCard(cardID uint) error {
 	if err != nil {
 		return fmt.Errorf("failed to set cart card: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var result APIResponse
 	if err := json.NewDecoder(resp.Body).Decode(&result); err != nil {
@@ -450,7 +466,7 @@ func (c *Client) ClearCart() error {
 	if err != nil {
 		return fmt.Errorf("failed to clear cart: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var result APIResponse
 	if err := json.NewDecoder(resp.Body).Decode(&result); err != nil {
@@ -468,7 +484,9 @@ func (c *Client) ClearCart() error {
 }
 
 // ConvertCart converts the cart into an order, charging the saved card.
-func (c *Client) ConvertCart() (*models.Order, error) {
+// Returns a CheckoutOutcome that either carries the completed Order or
+// indicates the customer must complete 3DS authentication via RedirectURL.
+func (c *Client) ConvertCart() (*CheckoutOutcome, error) {
 	url := fmt.Sprintf("%s/api/v1/cart/convert", c.BaseURL)
 
 	req, err := http.NewRequest("POST", url, nil)
@@ -480,7 +498,7 @@ func (c *Client) ConvertCart() (*models.Order, error) {
 	if err != nil {
 		return nil, fmt.Errorf("failed to convert cart: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var convertResp ConvertCartResponse
 	if err := json.NewDecoder(resp.Body).Decode(&convertResp); err != nil {
@@ -494,7 +512,107 @@ func (c *Client) ConvertCart() (*models.Order, error) {
 		return nil, fmt.Errorf("failed to convert cart")
 	}
 
-	return &convertResp.Data.Order, nil
+	if convertResp.Data.Status == "requires_action" {
+		return &CheckoutOutcome{
+			OrderID:        convertResp.Data.OrderID,
+			RequiresAction: true,
+			RedirectURL:    convertResp.Data.RedirectURL,
+		}, nil
+	}
+
+	if convertResp.Data.Order == nil {
+		return nil, fmt.Errorf("malformed convert response: missing order")
+	}
+	return &CheckoutOutcome{
+		Order:   convertResp.Data.Order,
+		OrderID: convertResp.Data.Order.ID,
+	}, nil
+}
+
+type OrderStatusResponse struct {
+	Success bool `json:"success"`
+	Data    struct {
+		ID     uint   `json:"id"`
+		Status string `json:"status"`
+	} `json:"data"`
+	Error *APIError `json:"error,omitempty"`
+}
+
+func (c *Client) GetOrderStatus(id uint) (string, error) {
+	url := fmt.Sprintf("%s/api/v1/orders/%d/status", c.BaseURL, id)
+	req, err := http.NewRequest("GET", url, nil)
+	if err != nil {
+		return "", fmt.Errorf("failed to create request: %w", err)
+	}
+	resp, err := c.doRequest(req)
+	if err != nil {
+		return "", fmt.Errorf("failed to fetch order status: %w", err)
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	var sResp OrderStatusResponse
+	if err := json.NewDecoder(resp.Body).Decode(&sResp); err != nil {
+		return "", fmt.Errorf("failed to decode order status response: %w", err)
+	}
+	if !sResp.Success {
+		if sResp.Error != nil {
+			return "", fmt.Errorf("%s: %s", sResp.Error.Code, sResp.Error.Message)
+		}
+		return "", fmt.Errorf("failed to fetch order status")
+	}
+	return sResp.Data.Status, nil
+}
+
+// RetryAuthOutcome is the result of POST /orders/{id}/retry-auth.
+// status=="requires_action" -> RedirectURL is a fresh QR target; resume polling.
+// Status=="succeeded" -> stripe approved frictionless; keep polling for the
+// webhook to flip status=paid (RedirectURL will be empty)
+type RetryAuthOutcome struct {
+	OrderID     uint
+	Status      string
+	RedirectURL string
+}
+
+type retryAuthResponse struct {
+	Success bool `json:"success"`
+	Data    struct {
+		OrderID     uint   `json:"order_id"`
+		Status      string `json:"status"`
+		RedirectURL string `json:"redirect_url,omitempty"`
+	} `json:"data"`
+	Error *APIError `json:"error,omitempty"`
+}
+
+// RetryAuth asks the server to re-Confirm the existing PaymentIntent for the
+// order, producing a new 3DS challenge URL. Used by the TUI's authFailed
+// screen so the customer can recover without re-entering the checkout flow.
+func (c *Client) RetryAuth(orderID uint) (*RetryAuthOutcome, error) {
+	url := fmt.Sprintf("%s/api/v1/orders/%d/retry-auth", c.BaseURL, orderID)
+	req, err := http.NewRequest("POST", url, nil)
+	if err != nil {
+		return nil, fmt.Errorf("failed to create retry request: %w", err)
+	}
+	resp, err := c.doRequest(req)
+	if err != nil {
+		return nil, fmt.Errorf("failed to send retry request: %w", err)
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	var rResp retryAuthResponse
+	if err := json.NewDecoder(resp.Body).Decode(&rResp); err != nil {
+		return nil, fmt.Errorf("failed to decode retry response: %w", err)
+	}
+	if !rResp.Success {
+		if rResp.Error != nil {
+			return nil, fmt.Errorf("%s: %s", rResp.Error.Code, rResp.Error.Message)
+		}
+		return nil, fmt.Errorf("failed to retry authentication")
+	}
+	return &RetryAuthOutcome{
+		OrderID:     rResp.Data.OrderID,
+		Status:      rResp.Data.Status,
+		RedirectURL: rResp.Data.RedirectURL,
+	}, nil
 }
 
 // GetCards fetches all saved cards for the user.
@@ -510,7 +628,7 @@ func (c *Client) GetCards() ([]models.Card, error) {
 	if err != nil {
 		return nil, fmt.Errorf("failed to fetch cards: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var cardsResp CardsResponse
 	if err := json.NewDecoder(resp.Body).Decode(&cardsResp); err != nil {
@@ -553,7 +671,7 @@ func (c *Client) SaveCard(params SaveCardRequest) (*models.Card, error) {
 	if err != nil {
 		return nil, fmt.Errorf("failed to save card: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var cardResp CardResponse
 	if err := json.NewDecoder(resp.Body).Decode(&cardResp); err != nil {
@@ -590,11 +708,11 @@ func (c *Client) CollectCard() (string, error) {
 	if err != nil {
 		return "", fmt.Errorf("failed to collect card: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var collectResp CollectCardResponse
 	if err := json.NewDecoder(resp.Body).Decode(&collectResp); err != nil {
-		return "", fmt.Errorf("failed to devode collect response: %w", err)
+		return "", fmt.Errorf("failed to decode collect response: %w", err)
 	}
 
 	if !collectResp.Success {
@@ -619,7 +737,7 @@ func (c *Client) DeleteCard(id uint) error {
 	if err != nil {
 		return fmt.Errorf("failed to delete card: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	if resp.StatusCode != http.StatusOK {
 		return fmt.Errorf("delete card failed with status %d", resp.StatusCode)
@@ -628,64 +746,6 @@ func (c *Client) DeleteCard(id uint) error {
 	return nil
 }
 
-type SSHKeyResponse struct {
-	Success bool `json:"success"`
-	Data    struct {
-		SSHKeys []models.SSHKey `json:"ssh_keys"`
-	} `json:"data"`
-	Error *APIError `json:"error,omitempty"`
-}
-
-func (c *Client) GetSSHKeys() ([]models.SSHKey, error) {
-	url := fmt.Sprintf("%s/api/v1/ssh-keys", c.BaseURL)
-
-	req, err := http.NewRequest("GET", url, nil)
-	if err != nil {
-		return nil, fmt.Errorf("failed to create request: %w", err)
-	}
-
-	resp, err := c.doRequest(req)
-	if err != nil {
-		return nil, fmt.Errorf("failed to fetch ssh keys: %w", err)
-	}
-	defer resp.Body.Close()
-
-	var keysResp SSHKeyResponse
-	if err := json.NewDecoder(resp.Body).Decode(&keysResp); err != nil {
-		return nil, fmt.Errorf("failed to decode ssh keys response: %w", err)
-	}
-
-	if !keysResp.Success {
-		if keysResp.Error != nil {
-			return nil, fmt.Errorf("%s: %s", keysResp.Error.Code, keysResp.Error.Message)
-		}
-		return nil, fmt.Errorf("failed to fetch ssh keys")
-	}
-	return keysResp.Data.SSHKeys, nil
-
-}
-
-func (c *Client) DeleteSSHKey(id uint) error {
-	url := fmt.Sprintf("%s/api/v1/ssh-keys/%d", c.BaseURL, id)
-
-	req, err := http.NewRequest("DELETE", url, nil)
-	if err != nil {
-		return fmt.Errorf("failed to create delete request: %w", err)
-	}
-
-	resp, err := c.doRequest(req)
-	if err != nil {
-		return fmt.Errorf("failed to delete ssh key: %w", err)
-	}
-	defer resp.Body.Close()
-
-	if resp.StatusCode != http.StatusOK {
-		return fmt.Errorf("delete ssh key failed with status %d", resp.StatusCode)
-	}
-
-	return nil
-}
-
 type OrderResponse struct {
 	Success bool `json:"success"`
 	Data    struct {
@@ -694,6 +754,20 @@ type OrderResponse struct {
 	Error *APIError `json:"error,omitempty"`
 }
 
+// RefundRequest is the customer-facing refund request payload.
+type RefundRequest struct {
+	Reason  string `json:"reason"`
+	Message string `json:"message"`
+}
+
+type refundRequestResponse struct {
+	Success bool `json:"success"`
+	Data    struct {
+		Status string `json:"status"`
+	} `json:"data"`
+	Error *APIError `json:"error,omitempty"`
+}
+
 func (c *Client) GetOrders() ([]models.Order, error) {
 	url := fmt.Sprintf("%s/api/v1/orders", c.BaseURL)
 
@@ -706,7 +780,7 @@ func (c *Client) GetOrders() ([]models.Order, error) {
 	if err != nil {
 		return nil, fmt.Errorf("failed to fetch orders: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var ordersResp OrderResponse
 	if err := json.NewDecoder(resp.Body).Decode(&ordersResp); err != nil {
@@ -722,6 +796,42 @@ func (c *Client) GetOrders() ([]models.Order, error) {
 	return ordersResp.Data.Orders, nil
 }
 
+// CreateRefundRequest posts a refund request for an order.
+func (c *Client) CreateRefundRequest(orderID uint, params RefundRequest) error {
+	url := fmt.Sprintf("%s/api/v1/orders/%d/refund-request", c.BaseURL, orderID)
+
+	jsonData, err := json.Marshal(params)
+	if err != nil {
+		return fmt.Errorf("failed to marshal refund request: %w", err)
+	}
+
+	req, err := http.NewRequest("POST", url, bytes.NewBuffer(jsonData))
+	if err != nil {
+		return fmt.Errorf("failed to create refund request: %w", err)
+	}
+	req.Header.Set("Content-Type", "application/json")
+
+	resp, err := c.doRequest(req)
+	if err != nil {
+		return fmt.Errorf("failed to send refund request: %w", err)
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	var refundResp refundRequestResponse
+	if err := json.NewDecoder(resp.Body).Decode(&refundResp); err != nil {
+		return fmt.Errorf("failed to decode refund response: %w", err)
+	}
+
+	if !refundResp.Success {
+		if refundResp.Error != nil {
+			return fmt.Errorf("%s: %s", refundResp.Error.Code, refundResp.Error.Message)
+		}
+		return fmt.Errorf("failed to send refund request")
+	}
+
+	return nil
+}
+
 // The Addresses API response
 type AddressResponse struct {
 	Success bool `json:"success"`
@@ -744,7 +854,7 @@ func (c *Client) GetAddresses() ([]models.Address, error) {
 		return nil, fmt.Errorf("failed to fetch addresses: %w", err)
 	}
 
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var addrResp AddressResponse
 	if err := json.NewDecoder(resp.Body).Decode(&addrResp); err != nil {
@@ -790,7 +900,7 @@ func (c *Client) CreateAddress(addrReq CreateAddressRequest) (*models.Address, e
 	if err != nil {
 		return nil, fmt.Errorf("failed to create address: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	var result struct {
 		Success bool `json:"success"`
@@ -827,7 +937,7 @@ func (c *Client) DeleteAddress(id uint) error {
 	if err != nil {
 		return fmt.Errorf("failed to delete address: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	if resp.StatusCode != http.StatusOK {
 		return fmt.Errorf("delete address failed with status %d", resp.StatusCode)
@@ -842,7 +952,6 @@ type ViewInitData struct {
 	Cart      []CartItemData    `json:"cart"`
 	Addresses []models.Address  `json:"addresses"`
 	Cards     []models.Card     `json:"cards"`
-	SSHKeys   []models.SSHKey   `json:"ssh_keys"`
 	Orders    []models.Order    `json:"orders"`
 }
 
@@ -863,7 +972,7 @@ func (c *Client) GetViewInit() (ViewInitData, error) {
 	if err != nil {
 		return ViewInitData{}, fmt.Errorf("view init request failed: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 	if resp.StatusCode != http.StatusOK {
 		return ViewInitData{}, fmt.Errorf("view init returned status: %d", resp.StatusCode)
 	}

pkg/api/doc.go

@@ -0,0 +1,3 @@
+// Package api is the client side of the house: it talks to our HTTP backend
+// so other Go code doesn't have to hand-roll requests.
+package api

pkg/audit/audit.go

@@ -1,124 +1,382 @@
-// Package audit writes structured JSON logs for financial events.
+// Package audit writes structured logs for financial events.
 // Every card addition, order creation, payment, and refund is recorded here.
 // Pipe this output to your log aggregator (Datadog, Loki, CloudWatch, etc.).
 package audit
 
 import (
 	"encoding/json"
-	"log"
-	"time"
+	"fmt"
+	"log/slog"
+
+	"terminalShop/pkg/models"
+
+	"gorm.io/gorm"
 )
 
+// EventOrderRequiresAction is the audit event-type string emitted whenever a
+// PaymentIntent is pushed into requires_action. Exposed so cart-flow handler
+// can count retry attempts without hardcoding the string literal.
+const EventOrderRequiresAction = "order_requires_action"
+
+// EventOrder3DSAbandoned is the audit event-type string emitted by the
+// abandoned-3DS sweep when it flips a stale requires_action row to failed.
+// Distinct from EventOrderRequiresAction (caveat #17) so the retry-cap count
+// stays decoupled from sweep activity
+const EventOrder3DSAbandoned = "order_3ds_abandoned"
+
+// EventCartRejected is the audit event-type string emitted when the per-order
+// spend cap blocks a checkout BEFORE an order row is created. The event lives
+// in slog only, persist() no-ops on zero order id, which is the correct shape
+// here (cap rejection is upstream of order state). See caveat #13.
+const EventCartRejected = "cart_rejected"
+
 type eventType string
 
 const (
-	eventCardAdded       eventType = "card_added"
-	eventCardDeleted     eventType = "card_deleted"
-	eventOrderCreated    eventType = "order_created"
-	eventOrderPaid       eventType = "order_paid"
-	eventOrderFailed     eventType = "order_failed"
-	eventOrderRefunded   eventType = "order_refunded"
-	eventPaymentCritical eventType = "payment_critical"
+	eventCardAdded              eventType = "card_added"
+	eventCardDeleted            eventType = "card_deleted"
+	eventCardExpired            eventType = "card_expired"
+	eventOrderCreated           eventType = "order_created"
+	eventOrderPaid              eventType = "order_paid"
+	eventOrderShipped           eventType = "order_shipped"
+	eventOrderFailed            eventType = "order_failed"
+	eventOrderRequiresAction    eventType = EventOrderRequiresAction
+	eventOrder3DSAbandoned      eventType = EventOrder3DSAbandoned
+	eventCartRejected           eventType = EventCartRejected
+	eventOrderRefunded          eventType = "order_refunded"
+	eventPaymentCritical        eventType = "payment_critical"
+	eventLabelPurchased         eventType = "label_purchased"
+	eventLabelOrphaned          eventType = "label_orphaned"
+	eventTrackingUpdated        eventType = "tracking_updated"
+	eventOrderDelivered         eventType = "order_delivered"
+	eventTrackingMarkedManually eventType = "tracking_marked_manually"
 )
 
 type event struct {
-	Time      time.Time         `json:"time"`
-	Event     eventType         `json:"event"`
-	UserID    uint              `json:"user_id,omitempty"`
-	OrderID   uint              `json:"order_id,omitempty"`
-	CardID    uint              `json:"card_id,omitempty"`
-	Amount    int               `json:"amount_cents,omitempty"`
-	StripeID  string            `json:"stripe_id,omitempty"`
-	CardLast4 string            `json:"card_last4,omitempty"`
-	CardBrand string            `json:"card_brand,omitempty"`
-	Error     string            `json:"error,omitempty"`
-	Extra     map[string]string `json:"extra,omitempty"`
+	Event      eventType
+	UserID     uint
+	OrderID    uint
+	CardID     uint
+	Amount     int
+	StripeID   string
+	CardLast4  string
+	CardBrand  string
+	Carrier    string
+	Tracking   string
+	Status     string
+	Error      string
+	Actor      string
+	TotalCents int
+	CapCents   int
 }
 
-func emit(e event) {
-	e.Time = time.Now().UTC()
-	b, err := json.Marshal(e)
-	if err != nil {
-		log.Printf("[audit] failed to marshal event: %v", err)
-		return
+func (e event) attrs() []any {
+	a := []any{"event", string(e.Event)}
+	if e.UserID != 0 {
+		a = append(a, "user_id", e.UserID)
 	}
-	log.Printf("[AUDIT] %s", b)
+	if e.OrderID != 0 {
+		a = append(a, "order_id", e.OrderID)
+	}
+	if e.CardID != 0 {
+		a = append(a, "card_id", e.CardID)
+	}
+	if e.Amount != 0 {
+		a = append(a, "amount_cents", e.Amount)
+	}
+	if e.StripeID != "" {
+		a = append(a, "stripe_id", e.StripeID)
+	}
+	if e.CardLast4 != "" {
+		a = append(a, "card_last4", e.CardLast4)
+	}
+	if e.CardBrand != "" {
+		a = append(a, "card_brand", e.CardBrand)
+	}
+	if e.Carrier != "" {
+		a = append(a, "carrier", e.Carrier)
+	}
+	if e.Tracking != "" {
+		a = append(a, "tracking", e.Tracking)
+	}
+	if e.Status != "" {
+		a = append(a, "status", e.Status)
+	}
+	if e.Error != "" {
+		a = append(a, "error", e.Error)
+	}
+	if e.Actor != "" {
+		a = append(a, "actor", e.Actor)
+	}
+	if e.TotalCents != 0 {
+		a = append(a, "total_cents", e.TotalCents)
+	}
+	if e.CapCents != 0 {
+		a = append(a, "cap_cents", e.CapCents)
+	}
+	return a
 }
 
 // CardAdded records that a user saved a new payment method.
 func CardAdded(userID, cardID uint, brand, last4 string) {
-	emit(event{
+	e := event{
 		Event:     eventCardAdded,
 		UserID:    userID,
 		CardID:    cardID,
 		CardBrand: brand,
 		CardLast4: last4,
-	})
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(0, eventCardAdded, e)
 }
 
 // CardDeleted records that a user removed a saved payment method.
 func CardDeleted(userID, cardID uint) {
-	emit(event{
+	e := event{
 		Event:  eventCardDeleted,
 		UserID: userID,
 		CardID: cardID,
-	})
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(0, eventCardDeleted, e)
+}
+
+// CardExpired records that a saved payment method expired from inactivity
+func CardExpired(userID, cardID uint) {
+	e := event{
+		Event:  eventCardExpired,
+		UserID: userID,
+		CardID: cardID,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(0, eventCardExpired, e)
 }
 
 // OrderCreated records that an order record was created (before payment).
 func OrderCreated(userID, orderID uint, amountCents int) {
-	emit(event{
+	e := event{
 		Event:   eventOrderCreated,
 		UserID:  userID,
 		OrderID: orderID,
 		Amount:  amountCents,
-	})
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventOrderCreated, e)
 }
 
 // OrderPaid records a successful charge.
 func OrderPaid(userID, orderID uint, amountCents int, stripePaymentIntentID string) {
-	emit(event{
+	e := event{
 		Event:    eventOrderPaid,
 		UserID:   userID,
 		OrderID:  orderID,
 		Amount:   amountCents,
 		StripeID: stripePaymentIntentID,
-	})
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventOrderPaid, e)
 }
 
-// OrderFailed records a failed charge attempt.
+// OrderShipped records that an order has been marked as shipped with carrier metadata
+func OrderShipped(userID, orderID uint, carrier, trackingNumber string) {
+	e := event{
+		Event:    eventOrderShipped,
+		UserID:   userID,
+		OrderID:  orderID,
+		Carrier:  carrier,
+		Tracking: trackingNumber,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventOrderShipped, e)
+}
+
+// OrderFailed records a failed charge attempt. Logged at WARN.
 func OrderFailed(userID, orderID uint, amountCents int, reason string) {
-	emit(event{
+	e := event{
 		Event:   eventOrderFailed,
 		UserID:  userID,
 		OrderID: orderID,
 		Amount:  amountCents,
 		Error:   reason,
-	})
+	}
+	slog.Warn("audit", e.attrs()...)
+	persist(orderID, eventOrderFailed, e)
 }
 
 // OrderRefunded records a refund.
 func OrderRefunded(userID, orderID uint, amountCents int, stripeRefundID string) {
-	emit(event{
+	e := event{
 		Event:    eventOrderRefunded,
 		UserID:   userID,
 		OrderID:  orderID,
 		Amount:   amountCents,
 		StripeID: stripeRefundID,
-	})
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventOrderRefunded, e)
 }
 
 // PaymentCritical records the dangerous state where Stripe charged the card
 // but the local database transaction failed. This MUST be investigated and
-// manually reconciled. Emit a loud log line that monitoring can alert on.
+// manually reconciled. Logged at ERROR so monitoring can alert on it.
 func PaymentCritical(orderID uint, stripePaymentIntentID string, err error) {
-	emit(event{
+	e := event{
 		Event:    eventPaymentCritical,
 		OrderID:  orderID,
 		StripeID: stripePaymentIntentID,
 		Error:    err.Error(),
-	})
-	// Second line so it's impossible to miss in plain-text log tails.
-	log.Printf("[AUDIT][CRITICAL] order %d was charged (pi=%s) but DB commit failed: %v — REQUIRES MANUAL RECONCILIATION",
-		orderID, stripePaymentIntentID, err)
+	}
+	slog.Error("audit", e.attrs()...)
+	persist(orderID, eventPaymentCritical, e)
+}
+
+func LabelPurchased(orderID uint, carrier, trackingNumber, shippoTxID string, costCents int) {
+	e := event{
+		Event:    eventLabelPurchased,
+		OrderID:  orderID,
+		Carrier:  carrier,
+		Tracking: trackingNumber,
+		StripeID: shippoTxID,
+		Amount:   costCents,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventLabelPurchased, e)
+}
+
+func LabelOrphaned(orderID uint, shippoTxID, trackingNumber string, err error) {
+	e := event{
+		Event:    eventLabelOrphaned,
+		OrderID:  orderID,
+		StripeID: shippoTxID,
+		Tracking: trackingNumber,
+		Error:    err.Error(),
+	}
+	slog.Error("audit", e.attrs()...)
+	persist(orderID, eventLabelOrphaned, e)
+}
+
+func TrackingUpdated(orderID uint, carrier, trackingNumber, status string) {
+	e := event{
+		Event:    eventTrackingUpdated,
+		OrderID:  orderID,
+		Carrier:  carrier,
+		Tracking: trackingNumber,
+		Status:   status,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventTrackingUpdated, e)
+}
+
+func OrderDelivered(orderID uint, trackingNumber string) {
+	e := event{
+		Event:    eventOrderDelivered,
+		OrderID:  orderID,
+		Tracking: trackingNumber,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventOrderDelivered, e)
+}
+
+// TrackingMarkedManually records operator made tracking status mark
+// from the slack interactivity surface. Actor is the slack username that
+// clicked the button
+func TrackingMarkedManually(orderID uint, status, actor string) {
+	e := event{
+		Event:   eventTrackingMarkedManually,
+		OrderID: orderID,
+		Status:  status,
+		Actor:   actor,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventTrackingMarkedManually, e)
+}
+
+// db is the optional persistence target. nil = slog-only.
+// set once at startup with SetDB, funcs stay slog-primary regardless.
+var db *gorm.DB
+
+// SetDB wires the audit package to a database for persistent event rows.
+// call once after database.Migrate. Audit funcs still write slog when
+// db is nil, so tests don't need to wire this.
+func SetDB(d *gorm.DB) { db = d }
+
+func persist(orderID uint, t eventType, e event) {
+	if db == nil || orderID == 0 {
+		return
+	}
+	actor := e.Actor
+	if actor == "" {
+		if e.UserID > 0 {
+			actor = fmt.Sprintf("user:%d", e.UserID)
+		} else {
+			actor = "system"
+		}
+	}
+	payload, err := json.Marshal(attrsToMap(e.attrs()))
+	if err != nil {
+		slog.Error("audit persist marshal", "error", err, "event", string(t))
+		return
+	}
+	row := &models.OrderEvent{
+		OrderID: orderID,
+		Type:    string(t),
+		Payload: string(payload),
+		Actor:   actor,
+	}
+	if err := db.Create(row).Error; err != nil {
+		slog.Error("audit persist write", "error", err, "event", string(t), "order_id", orderID)
+	}
+}
+
+func attrsToMap(a []any) map[string]any {
+	m := make(map[string]any, len(a)/2)
+	for i := 0; i+1 < len(a); i += 2 {
+		k, ok := a[i].(string)
+		if !ok {
+			continue
+		}
+		m[k] = a[i+1]
+	}
+	return m
+}
+
+func OrderRequiresAction(userID, orderID uint, paymentIntentID string) {
+	e := event{
+		Event:    eventOrderRequiresAction,
+		UserID:   userID,
+		OrderID:  orderID,
+		StripeID: paymentIntentID,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventOrderRequiresAction, e)
+}
+
+// Order3DSAbandoned records the abandoned-3DS sweep flipping a stale
+// requires_action row to failed because Stripe still reports the underlying
+// PaymentIntent as outstanding past the sweep threshold.
+func Order3DSAbandoned(userID, orderID uint, paymentIntentID string) {
+	e := event{
+		Event:    eventOrder3DSAbandoned,
+		UserID:   userID,
+		OrderID:  orderID,
+		StripeID: paymentIntentID,
+	}
+	slog.Info("audit", e.attrs()...)
+	persist(orderID, eventOrder3DSAbandoned, e)
+}
+
+// CartRejected records the per-order cap blocking a checkout BEFORE an
+// order row is created. Slog-only by design: cap rejection runs upstream
+// of order creation so there is no order id to scope a persistent
+// OrderEvent row. persist() is intentionally not called - future refactors
+// of the persist() zero-id guard must not silently start writing rows here.
+// Counterpart to the validation_over_limit Prometheus counter.
+func CartRejected(userID uint, totalCents, capCents int) {
+	e := event{
+		Event:      eventCartRejected,
+		UserID:     userID,
+		TotalCents: totalCents,
+		CapCents:   capCents,
+	}
+	slog.Info("audit", e.attrs()...)
 }

pkg/audit/audit_test.go

@@ -0,0 +1,41 @@
+package audit
+
+import (
+	"bytes"
+	"encoding/json"
+	"log/slog"
+	"strings"
+	"testing"
+)
+
+func TestCartRejected(t *testing.T) {
+	var buf bytes.Buffer
+	prev := slog.Default()
+	slog.SetDefault(slog.New(slog.NewJSONHandler(&buf, nil)))
+	t.Cleanup(func() { slog.SetDefault(prev) })
+
+	CartRejected(42, 25000, 20000)
+
+	raw := strings.TrimSpace(buf.String())
+	if raw == "" {
+		t.Fatalf("CartRejected: no slog output captured")
+	}
+
+	var rec map[string]any
+	if err := json.Unmarshal([]byte(raw), &rec); err != nil {
+		t.Fatalf("decode slog record: %v\nraw: %s", err, raw)
+	}
+
+	if got, want := rec["event"], "cart_rejected"; got != want {
+		t.Errorf("event: want %q, got %v", want, got)
+	}
+	if n, _ := rec["user_id"].(float64); int(n) != 42 {
+		t.Errorf("user_id want 42, got %v", rec["user_id"])
+	}
+	if n, _ := rec["total_cents"].(float64); int(n) != 25000 {
+		t.Errorf("total_cents: want 25000, got %v", rec["total_cents"])
+	}
+	if n, _ := rec["cap_cents"].(float64); int(n) != 20000 {
+		t.Errorf("cap_cents: want 20000, got %v", rec["cap_cents"])
+	}
+}

pkg/auth/doc.go

@@ -0,0 +1,3 @@
+// Package auth sorts out who you are: logging in with an SSH key and minting
+// the JWT you carry around afterwards.
+package auth

pkg/auth/jwt.go

@@ -53,7 +53,7 @@ func (m *JWTManager) GenerateToken(userID uint, email, username string) (string,
 
 // ValidateToken validates a JWT token and returns the claims
 func (m *JWTManager) ValidateToken(tokenString string) (*Claims, error) {
-	token, err := jwt.ParseWithClaims(tokenString, &Claims{}, func(token *jwt.Token) (interface{}, error) {
+	token, err := jwt.ParseWithClaims(tokenString, &Claims{}, func(token *jwt.Token) (any, error) {
 		// Verify signing method
 		if _, ok := token.Method.(*jwt.SigningMethodHMAC); !ok {
 			return nil, fmt.Errorf("unexpected signing method: %v", token.Header["alg"])

pkg/auth/ssh_auth_test.go

@@ -17,7 +17,7 @@ import (
 func setupAuthTestDB(t *testing.T) string {
 	t.Helper()
 	testDB := "test_ssh_auth.db"
-	os.Remove(testDB)
+	_ = os.Remove(testDB)
 	database.ResetForTesting()
 
 	db, err := database.Connect(testDB)
@@ -47,7 +47,7 @@ func newTestSSHKey(t *testing.T) gossh.PublicKey {
 
 func TestAuthenticateSSHKeyNewUser(t *testing.T) {
 	testDB := setupAuthTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -72,7 +72,7 @@ func TestAuthenticateSSHKeyNewUser(t *testing.T) {
 
 func TestAuthenticateSSHKeyExistingUser(t *testing.T) {
 	testDB := setupAuthTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -96,7 +96,7 @@ func TestAuthenticateSSHKeyExistingUser(t *testing.T) {
 
 func TestRegisterWithSSHKey(t *testing.T) {
 	testDB := setupAuthTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -121,7 +121,7 @@ func TestRegisterWithSSHKey(t *testing.T) {
 
 func TestRegisterWithSSHKeyDuplicate(t *testing.T) {
 	testDB := setupAuthTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -145,7 +145,7 @@ func TestRegisterWithSSHKeyDuplicate(t *testing.T) {
 
 func TestIsSSHKeyRegistered(t *testing.T) {
 	testDB := setupAuthTestDB(t)
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer database.ResetForTesting()
 
 	db := database.GetDB()
@@ -164,7 +164,7 @@ func TestIsSSHKeyRegistered(t *testing.T) {
 	}
 
 	// After authentication (which auto-creates)
-	svc.AuthenticateSSHKey(key)
+	_, _, _ = svc.AuthenticateSSHKey(key)
 
 	registered, err = svc.IsSSHKeyRegistered(key)
 	if err != nil {

pkg/bring/booking.go

@@ -0,0 +1,253 @@
+package bring
+
+import (
+	"bytes"
+	"context"
+	"encoding/json"
+	"fmt"
+	"io"
+	"net/http"
+	"os"
+	"terminalShop/pkg/shipping"
+	"time"
+
+	"go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp"
+)
+
+const bookingBaseURL = "https://api.bring.com/booking-api/api/booking"
+
+type BookingClient struct {
+	apiUID         string
+	apiKey         string
+	customerNumber string
+	testMode       bool
+	httpClient     *http.Client
+}
+
+func NewBookingClient(apiUID string, apiKey string, customerNumber string, testMode bool) *BookingClient {
+	return &BookingClient{
+		apiUID:         apiUID,
+		apiKey:         apiKey,
+		customerNumber: customerNumber,
+		testMode:       testMode,
+		httpClient: &http.Client{
+			Timeout:   20 * time.Second,
+			Transport: otelhttp.NewTransport(http.DefaultTransport),
+		},
+	}
+}
+
+type BookingAddress struct {
+	Name        string
+	Street1     string
+	Street2     string
+	City        string
+	Country     string
+	Zip         string
+	Phone       string
+	Email       string
+	ContactName string
+}
+
+type LineItem struct {
+	Title    string
+	Quantity int
+	WeightKg float64
+}
+
+func (c *BookingClient) CreateLabel(ctx context.Context, to BookingAddress, email string, items []LineItem) (*shipping.LabelResult, error) {
+	from := fromAddressNO()
+	if from.Street1 == "" {
+		return nil, fmt.Errorf("SHIP_FROM_NO_STREET1 not configured")
+	}
+	if c.customerNumber == "" {
+		return nil, fmt.Errorf("BRING_CUSTOMER_NUMBER not configured")
+	}
+
+	totalKg := 0.0
+	for _, item := range items {
+		totalKg += float64(item.Quantity) * item.WeightKg
+	}
+	if totalKg <= 0 {
+		return nil, fmt.Errorf("order has zero shipping weight")
+	}
+
+	oslo, err := time.LoadLocation("Europe/Oslo")
+	if err != nil {
+		oslo = time.UTC
+	}
+	shippingAt := time.Now().In(oslo).Add(1 * time.Hour).Format("2006-01-02T15:04:05-07:00")
+
+	payload := map[string]any{
+		"testIndicator": c.testMode,
+		"schemaVersion": 1,
+		"consignments": []map[string]any{{
+			"shippingDateTime": shippingAt,
+			"parties": map[string]any{
+				"sender":    partyPayload(from, ""),
+				"recipient": partyPayload(to, email),
+			},
+			"product": map[string]any{
+				"id":             "SERVICEPAKKE",
+				"customerNumber": c.customerNumber,
+			},
+			"packages": []map[string]any{{
+				"weightInKg":       roundN(totalKg, 3),
+				"goodsDescription": "Roasted coffee beans",
+				"dimensions": map[string]any{
+					"heightInCm": 30,
+					"widthInCm":  30,
+					"lengthInCm": 30,
+				},
+			}},
+		}},
+	}
+
+	var resp bookingResponse
+	if err := c.doJSON(ctx, bookingBaseURL, payload, &resp); err != nil {
+		return nil, err
+	}
+	if len(resp.Consignments) == 0 {
+		return nil, fmt.Errorf("bring returned no consignments")
+	}
+	c0 := resp.Consignments[0]
+	if c0.Confirmation == nil {
+		return nil, fmt.Errorf("bring booking failed: %s", firstError(c0.Errors))
+	}
+
+	confirmation := c0.Confirmation
+	if len(confirmation.Packages) == 0 || confirmation.Packages[0].TrackingNumber == "" {
+		return nil, fmt.Errorf("bring confirmation missing tracking number")
+	}
+
+	labelURL := ""
+	if confirmation.Links != nil {
+		labelURL = confirmation.Links.Labels
+	}
+
+	tracking := confirmation.Packages[0].TrackingNumber
+	trackingURL := fmt.Sprintf("https://sporing.posten.no/sporing/%s", tracking)
+
+	return &shipping.LabelResult{
+		TransactionID:  confirmation.ConsignmentNumber,
+		Carrier:        "BRING",
+		ServiceLevel:   "SERVICEPAKKE",
+		TrackingNumber: tracking,
+		TrackingURL:    trackingURL,
+		LabelURL:       labelURL,
+		CostCents:      0,
+	}, nil
+
+}
+
+type bookingResponse struct {
+	Consignments []struct {
+		Confirmation *struct {
+			ConsignmentNumber string `json:"consignmentNumber"`
+			Links             *struct {
+				Labels string `json:"labels"`
+			} `json:"links"`
+			Packages []struct {
+				CorrelationID  string `json:"correlationId"`
+				TrackingNumber string `json:"trackingNumber"`
+			} `json:"packages"`
+		} `json:"confirmation"`
+		Errors []struct {
+			Messages []struct {
+				Code    string `json:"code"`
+				Message string `json:"message"`
+			} `json:"messages"`
+		} `json:"errors"`
+	} `json:"consignments"`
+}
+
+func firstError(errs []struct {
+	Messages []struct {
+		Code    string `json:"code"`
+		Message string `json:"message"`
+	} `json:"messages"`
+}) string {
+	if len(errs) == 0 || len(errs[0].Messages) == 0 {
+		return "no detail"
+	}
+	return errs[0].Messages[0].Message
+}
+
+func (c *BookingClient) doJSON(ctx context.Context, url string, body any, out any) error {
+	b, err := json.Marshal(body)
+	if err != nil {
+		return fmt.Errorf("marshal: %w", err)
+	}
+	req, err := http.NewRequestWithContext(ctx, "POST", url, bytes.NewReader(b))
+	if err != nil {
+		return fmt.Errorf("new request: %w", err)
+	}
+	req.Header.Set("Content-Type", "application/json")
+	req.Header.Set("Accept", "application/json")
+	req.Header.Set("X-Mybring-API-Uid", c.apiUID)
+	req.Header.Set("X-Mybring-API-Key", c.apiKey)
+	req.Header.Set("X-Mybring-API-Customer-Number", c.customerNumber)
+	clientURL := os.Getenv("BRING_CLIENT_URL")
+	if clientURL == "" {
+		clientURL = "https://sshops.uk"
+	}
+	req.Header.Set("X-Bring-Client-URL", clientURL)
+
+	resp, err := c.httpClient.Do(req)
+	if err != nil {
+		return fmt.Errorf("request: %w", err)
+	}
+	defer func() { _ = resp.Body.Close() }()
+	respBody, err := io.ReadAll(resp.Body)
+	if err != nil {
+		return fmt.Errorf("read response: %w", err)
+	}
+	if resp.StatusCode < 200 || resp.StatusCode >= 300 {
+		return fmt.Errorf("bring booking %d: %s", resp.StatusCode, string(respBody))
+	}
+	if err := json.Unmarshal(respBody, out); err != nil {
+		return fmt.Errorf("parse response: %w", err)
+	}
+	return nil
+}
+
+func roundN(v float64, n int) float64 {
+	pow := 1.0
+	for i := 0; i < n; i++ {
+		pow *= 10
+	}
+	if v >= 0 {
+		return float64(int64(v*pow+0.5)) / pow
+	}
+	return float64(int64(v*pow-0.5)) / pow
+}
+
+func partyPayload(a BookingAddress, email string) map[string]any {
+	m := map[string]any{
+		"name":        a.Name,
+		"addressLine": a.Street1,
+		"postalCode":  a.Zip,
+		"city":        a.City,
+		"countryCode": a.Country,
+	}
+	if a.Street2 != "" {
+		m["addressLine2"] = a.Street2
+	}
+	if email != "" || a.Phone != "" {
+		m["contact"] = map[string]any{"name": a.Name, "email": email, "phoneNumber": a.Phone}
+	}
+	return m
+}
+
+func fromAddressNO() BookingAddress {
+	return BookingAddress{
+		Name:    os.Getenv("SHIP_FROM_NO_NAME"),
+		Street1: os.Getenv("SHIP_FROM_NO_STREET1"),
+		Street2: os.Getenv("SHIP_FROM_NO_STREET2"),
+		City:    os.Getenv("SHIP_FROM_NO_CITY"),
+		Country: os.Getenv("SHIP_FROM_NO_COUNTRY"),
+		Zip:     os.Getenv("SHIP_FROM_NO_ZIP"),
+		Phone:   os.Getenv("SHIP_FROM_NO_PHONE"),
+		Email:   os.Getenv("SHIP_FROM_NO_EMAIL"),
+	}
+}

pkg/bring/bring.go

@@ -1,6 +1,7 @@
 package bring
 
 import (
+	"context"
 	"encoding/json"
 	"fmt"
 	"io"
@@ -9,6 +10,8 @@ import (
 	"regexp"
 	"strings"
 	"time"
+
+	"go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp"
 )
 
 const baseURL = "https://api.bring.com/address"
@@ -26,7 +29,8 @@ func NewClient(apiUID, apiKey string) *Client {
 		apiUID: apiUID,
 		apiKey: apiKey,
 		httpClient: &http.Client{
-			Timeout: 10 * time.Second,
+			Timeout:   10 * time.Second,
+			Transport: otelhttp.NewTransport(http.DefaultTransport),
 		},
 	}
 }
@@ -79,7 +83,7 @@ func parseStreet(street string) (name string, number string) {
 	return strings.TrimSpace(street), ""
 }
 
-func (c *Client) ValidateAddress(addr Address) (*Address, error) {
+func (c *Client) ValidateAddress(ctx context.Context, addr Address) (*Address, error) {
 	streetName, streetNumber := parseStreet(addr.Street1)
 
 	params := url.Values{}
@@ -93,7 +97,7 @@ func (c *Client) ValidateAddress(addr Address) (*Address, error) {
 
 	reqURL := fmt.Sprintf("%s/api/no/validation?%s", baseURL, params.Encode())
 
-	req, err := http.NewRequest("GET", reqURL, nil)
+	req, err := http.NewRequestWithContext(ctx, "GET", reqURL, nil)
 	if err != nil {
 		return nil, fmt.Errorf("failed to create request: %w", err)
 	}
@@ -106,7 +110,7 @@ func (c *Client) ValidateAddress(addr Address) (*Address, error) {
 	if err != nil {
 		return nil, fmt.Errorf("bring request failed: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	respBody, err := io.ReadAll(resp.Body)
 	if err != nil {

pkg/bring/doc.go

@@ -0,0 +1,3 @@
+// Package bring talks to Bring, the Norwegian postal service, for booking
+// shipments and printing labels.
+package bring

pkg/config/config.go

@@ -3,8 +3,10 @@ package config
 import (
 	"errors"
 	"fmt"
+	"log/slog"
 	"net/url"
 	"os"
+	"strconv"
 	"strings"
 
 	"github.com/joho/godotenv"
@@ -12,20 +14,26 @@ import (
 
 // Config holds all application configuration
 type Config struct {
-	APIPort             string
-	APIURL              string
-	AppURL              string
-	SSHPort             string
-	Environment         string
-	DatabaseURL         string
-	JWTSecret           string
-	StripeSecretKey     string
-	StripePublicKey     string
-	StripeWebhookSecret string
-	ShippoAPIKey        string
-	AuthFingerprintKey  string
-	BringAPIUID         string
-	BringAPIKey         string
+	APIPort                      string
+	APIURL                       string
+	AppURL                       string
+	SSHPort                      string
+	Environment                  string
+	DatabaseURL                  string
+	JWTSecret                    string
+	StripeSecretKey              string
+	StripePublicKey              string
+	StripeWebhookSecret          string
+	ShippoAPIKey                 string
+	AuthFingerprintKey           string
+	BringAPIUID                  string
+	BringAPIKey                  string
+	BringCustomerNumber          string
+	ShippoWebhookSecret          string
+	SlackSigningSecret           string
+	AdminAPIKey                  string
+	MaxOrderCents                int
+	Abandoned3DSThresholdMinutes int
 }
 
 // Load reads configuration from environment variables and validates required secrets.
@@ -44,20 +52,26 @@ func Load() (*Config, error) {
 	apiPort := getEnvOrDefault("API_PORT", "8080")
 	apiURL := getEnvOrDefault("API_URL", fmt.Sprintf("http://localhost:%s", apiPort))
 	cfg := &Config{
-		APIPort:             apiPort,
-		APIURL:              apiURL,
-		AppURL:              getEnvOrDefault("APP_URL", apiURL),
-		SSHPort:             getEnvOrDefault("SSH_PORT", "23457"),
-		Environment:         getEnvOrDefault("ENVIRONMENT", "development"),
-		DatabaseURL:         getEnvOrDefault("DATABASE_URL", "terminalshop.db"),
-		JWTSecret:           os.Getenv("JWT_SECRET"),
-		StripeSecretKey:     os.Getenv("STRIPE_SECRET_KEY"),
-		StripePublicKey:     os.Getenv("STRIPE_PUBLIC_KEY"),
-		StripeWebhookSecret: os.Getenv("STRIPE_WEBHOOK_SECRET"),
-		ShippoAPIKey:        os.Getenv("SHIPPO_API_KEY"),
-		AuthFingerprintKey:  os.Getenv("AUTH_FINGERPRINT_KEY"),
-		BringAPIUID:         os.Getenv("BRING_API_UID"),
-		BringAPIKey:         os.Getenv("BRING_API_KEY"),
+		APIPort:                      apiPort,
+		APIURL:                       apiURL,
+		AppURL:                       getEnvOrDefault("APP_URL", apiURL),
+		SSHPort:                      getEnvOrDefault("SSH_PORT", "23457"),
+		Environment:                  getEnvOrDefault("ENVIRONMENT", "development"),
+		DatabaseURL:                  getEnvOrDefault("DATABASE_URL", "terminalshop.db"),
+		JWTSecret:                    os.Getenv("JWT_SECRET"),
+		StripeSecretKey:              os.Getenv("STRIPE_SECRET_KEY"),
+		StripePublicKey:              os.Getenv("STRIPE_PUBLIC_KEY"),
+		StripeWebhookSecret:          os.Getenv("STRIPE_WEBHOOK_SECRET"),
+		ShippoAPIKey:                 os.Getenv("SHIPPO_API_KEY"),
+		AuthFingerprintKey:           os.Getenv("AUTH_FINGERPRINT_KEY"),
+		BringAPIUID:                  os.Getenv("BRING_API_UID"),
+		BringAPIKey:                  os.Getenv("BRING_API_KEY"),
+		BringCustomerNumber:          os.Getenv("BRING_CUSTOMER_NUMBER"),
+		ShippoWebhookSecret:          os.Getenv("SHIPPO_WEBHOOK_SECRET"),
+		SlackSigningSecret:           os.Getenv("SLACK_SIGNING_SECRET"),
+		AdminAPIKey:                  os.Getenv("ADMIN_API_KEY"),
+		MaxOrderCents:                loadMaxOrderCents(),
+		Abandoned3DSThresholdMinutes: loadAbandoned3DSThresholdMinutes(),
 	}
 
 	if err := cfg.validate(); err != nil {
@@ -78,6 +92,7 @@ func (c *Config) validate() error {
 		{"JWT_SECRET", c.JWTSecret},
 		{"STRIPE_SECRET_KEY", c.StripeSecretKey},
 		{"AUTH_FINGERPRINT_KEY", c.AuthFingerprintKey},
+		{"STRIPE_WEBHOOK_SECRET", c.StripeWebhookSecret},
 	}
 
 	var missing []string
@@ -122,3 +137,45 @@ func getEnvOrDefault(key, defaultValue string) string {
 	}
 	return defaultValue
 }
+
+// loadMaxOrderCents reads MAX_ORDER_CENTS. Default $500 — aligns with the
+// PSD2 TRA exemption ceiling (above this, Stripe always requests SCA, so the
+// cap is only meaningful below it). Explicit 0 disables the cap. Garbage or
+// negative values fall back to the default with a warning so an operator
+// typo cannot silently disable a fraud control.
+func loadMaxOrderCents() int {
+	const defaultCap = 50000
+	raw := os.Getenv("MAX_ORDER_CENTS")
+	if raw == "" {
+		return defaultCap
+	}
+	n, err := strconv.Atoi(raw)
+	if err != nil || n < 0 {
+		fmt.Printf("WARNING: MAX_ORDER_CENTS=%q invalid, falling back to default %d\n", raw, defaultCap)
+		return defaultCap
+	}
+	return n
+}
+
+// loadAbandoned3DSThresholdMinutes read ABANDONED_3DS_THRESHOLD_MINUTES.
+// The abandoned-3DS sweep only flips requires_action rows whose updated_at iconfigs
+// older than this many minutes. Default 30 min. Values below 1 fall back to
+// the default so a typo cannot collapse the grace window the TUI polls inside.
+func loadAbandoned3DSThresholdMinutes() int {
+	const defaultMinutes = 30
+	raw := os.Getenv("ABANDONED_3DS_THRESHOLD_MINUTES")
+	if raw == "" {
+		return defaultMinutes
+	}
+	n, err := strconv.Atoi(raw)
+	if err != nil || n < 1 {
+		slog.Warn("invalid ABANDONED_3DS_THRESHOLD_MINUTES, falling back",
+			"raw", raw, "default", defaultMinutes)
+		return defaultMinutes
+	}
+	if n < 10 {
+		slog.Warn("ABANDONED_3DS_THRESHOLD_MINUTES below 10 may race in-flight 3ds challenges",
+			"value", n)
+	}
+	return n
+}

pkg/config/config_test.go

@@ -0,0 +1,78 @@
+package config
+
+import (
+	"io"
+	"log/slog"
+	"os"
+	"testing"
+)
+
+// TestMain silences the package's slog warnings so the negative/garbage
+// env-var cases plus the sub-10 valid-minimum case don't spam test output.
+// The actual fall-back behavior is still asserted via the case tables.
+func TestMain(m *testing.M) {
+	prev := slog.Default()
+	slog.SetDefault(slog.New(slog.NewTextHandler(io.Discard, nil)))
+	code := m.Run()
+	slog.SetDefault(prev)
+	os.Exit(code)
+}
+
+func TestLoadMaxOrderCents(t *testing.T) {
+	cases := []struct {
+		name string
+		env  string // "" means unset
+		want int
+	}{
+		{"empty falls back to default", "", 50000},
+		{"explicit zero disables", "0", 0},
+		{"valid override", "30000", 30000},
+		{"negative falls back to default", "-1", 50000},
+		{"garbage falls back to default", "two hundred", 50000},
+		{"empty after trim falls back to default", "", 50000},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			if tc.env == "" {
+				t.Setenv("MAX_ORDER_CENTS", "")
+			} else {
+				t.Setenv("MAX_ORDER_CENTS", tc.env)
+			}
+			got := loadMaxOrderCents()
+			if got != tc.want {
+				t.Errorf("loadMaxOrderCents() = %d, want %d", got, tc.want)
+			}
+		})
+	}
+}
+
+// TestLoadAbandoned3DSThresholdMinutes covers the env-parsing surface for
+// the sweep threshold. Zero and negative fall back to the default (unlike
+// MaxOrderCents where zero is a deliberate off-switch) because a zero
+// threshold would sweep every requires_action row on the first tick and
+// race the customer's in-progress challenge.
+func TestLoadAbandoned3DSThresholdMinutes(t *testing.T) {
+	cases := []struct {
+		name string
+		env  string // "" means unset
+		want int
+	}{
+		{"empty falls back to default", "", 30},
+		{"valid override", "45", 45},
+		{"zero falls back to default", "0", 30},
+		{"negative falls back to default", "-5", 30},
+		{"garbage falls back to default", "half an hour", 30},
+		{"valid minimum (warns)", "1", 1},
+	}
+
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Setenv("ABANDONED_3DS_THRESHOLD_MINUTES", tc.env)
+			got := loadAbandoned3DSThresholdMinutes()
+			if got != tc.want {
+				t.Errorf("loadAbandoned3DSThresholdMinutes() = %d, want %d", got, tc.want)
+			}
+		})
+	}
+}

pkg/config/doc.go

@@ -0,0 +1,3 @@
+// Package config reads everything out of the environment so secrets and
+// settings stay out of the source code.
+package config

pkg/database/db.go

@@ -11,6 +11,8 @@ import (
 	"gorm.io/driver/sqlite"
 	"gorm.io/gorm"
 	"gorm.io/gorm/logger"
+
+	"gorm.io/plugin/opentelemetry/tracing"
 )
 
 var (
@@ -42,6 +44,14 @@ func Connect(dsn string) (*gorm.DB, error) {
 			return
 		}
 
+		if pluginErr := db.Use(tracing.NewPlugin(
+			tracing.WithoutMetrics(),
+			tracing.WithoutQueryVariables(),
+		)); pluginErr != nil {
+			err = fmt.Errorf("failed to register otel plugin: %w", pluginErr)
+			return
+		}
+
 		// Configure connection pool for PostgreSQL.
 		if isPostgres {
 			sqlDB, poolErr := db.DB()
@@ -91,7 +101,7 @@ func Close() error {
 // WARNING: Only use this in tests!
 func ResetForTesting() {
 	if db != nil {
-		Close()
+		_ = Close()
 		db = nil
 		once = sync.Once{}
 	}

pkg/database/db_test.go

@@ -10,7 +10,7 @@ import (
 func TestConnect(t *testing.T) {
 	// Use a temporary test database
 	testDB := "test_terminalshop.db"
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer ResetForTesting()
 
 	db, err := Connect(testDB)
@@ -35,7 +35,7 @@ func TestConnect(t *testing.T) {
 
 func TestMigrate(t *testing.T) {
 	testDB := "test_migrate.db"
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer ResetForTesting()
 
 	db, err := Connect(testDB)
@@ -57,7 +57,7 @@ func TestMigrate(t *testing.T) {
 
 func TestSeed(t *testing.T) {
 	testDB := "test_seed.db"
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer ResetForTesting()
 
 	db, err := Connect(testDB)
@@ -115,7 +115,7 @@ func TestSeed(t *testing.T) {
 
 func TestGetDB(t *testing.T) {
 	testDB := "test_getdb.db"
-	defer os.Remove(testDB)
+	defer func() { _ = os.Remove(testDB) }()
 	defer ResetForTesting()
 
 	// Initialize connection

pkg/database/doc.go

@@ -0,0 +1,3 @@
+// Package database opens the SQLite connection, runs the migrations, and
+// drops in some seed data so the shop isn't empty on a fresh boot.
+package database

pkg/database/migrate.go

@@ -3,9 +3,11 @@ package database
 import (
 	"fmt"
 	"log"
+	"time"
+
+	"terminalShop/pkg/models"
 
 	"gorm.io/gorm"
-	"terminalShop/pkg/models"
 )
 
 // Migrate runs database migrations
@@ -15,19 +17,32 @@ func Migrate(db *gorm.DB) error {
 	// AutoMigrate will create tables, missing columns, and indexes
 	// It will NOT delete unused columns or change column types
 	if err := db.AutoMigrate(
-		&models.Cart{},     // Server-side shipping cart
-		&models.CartItem{}, // Cart line items
-		&models.Coffee{},
+		&models.Cart{},      // Server-side shopping cart
+		&models.CartItem{},  // Cart line items
+		&models.Coffee{},    // Coffees
 		&models.User{},      // SSH key-based authentication
 		&models.Card{},      // Saved payment methods
 		&models.Order{},     // Completed purchases
 		&models.OrderItem{}, // Line items within orders
 		&models.Address{},   // Saved addresses
-		&models.SSHKey{},    // One of the users ssh keys
+		&models.OrderEvent{},
+		&models.PayRedirect{}, // short-token -> stripe url store (10 min TTL)
 	); err != nil {
 		return fmt.Errorf("migration failed: %w", err)
 	}
 
+	if err := backfillCardStorageExpiration(db); err != nil {
+		return err
+	}
+
 	log.Println("Database migrations completed successfully")
 	return nil
 }
+
+func backfillCardStorageExpiration(db *gorm.DB) error {
+	expiresAt := models.CardStorageExpiresAt(time.Now())
+	if err := db.Model(&models.Card{}).Where("storage_expires_at IS NULL").Update("storage_expires_at", expiresAt).Error; err != nil {
+		return fmt.Errorf("card storage ttl backfill failed: %w", err)
+	}
+	return nil
+}

pkg/database/migrate_test.go

@@ -0,0 +1,67 @@
+package database
+
+import (
+	"os"
+	"testing"
+	"time"
+
+	"terminalShop/pkg/models"
+)
+
+func TestBackfillCardStorageExpiration_FillsNullRowsOnly(t *testing.T) {
+	testDB := "test_backfill.db"
+	defer func() { _ = os.Remove(testDB) }()
+	defer ResetForTesting()
+
+	db, err := Connect(testDB)
+	if err != nil {
+		t.Fatalf("connect: %v", err)
+	}
+	if err := Migrate(db); err != nil {
+		t.Fatalf("migrate: %v", err)
+	}
+
+	user := models.User{
+		SSHKeyFingerprint: "SHA256:backfill",
+		SSHPublicKey:      "ssh-ed25519 AAAA backfill",
+		Name:              "Backfill",
+		Email:             "backfill@example.com",
+	}
+	if err := db.Create(&user).Error; err != nil {
+		t.Fatalf("seed user: %v", err)
+	}
+
+	legacy := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_legacy", Last4: "0000",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030,
+	}
+	if err := db.Create(&legacy).Error; err != nil {
+		t.Fatalf("seed legacy: %v", err)
+	}
+
+	fixed := time.Date(2030, 1, 1, 0, 0, 0, 0, time.UTC)
+	preset := models.Card{
+		UserID: user.ID, StripePaymentID: "pm_preset", Last4: "9999",
+		Brand: "Visa", ExpMonth: 1, ExpYear: 2030, StorageExpiresAt: &fixed,
+	}
+	if err := db.Create(&preset).Error; err != nil {
+		t.Fatalf("ssed preset: %v", err)
+	}
+	if err := backfillCardStorageExpiration(db); err != nil {
+		t.Fatalf("seed preset: %v", err)
+	}
+
+	var reloadedLegacy, reloadedPreset models.Card
+	if err := db.First(&reloadedLegacy, legacy.ID).Error; err != nil {
+		t.Fatalf("reload legacy: %v", err)
+	}
+	if err := db.First(&reloadedPreset, preset.ID).Error; err != nil {
+		t.Fatalf("reload preset: %v", err)
+	}
+	if reloadedLegacy.StorageExpiresAt == nil {
+		t.Fatalf("legacy card storage_expires_at still NULL after backfill")
+	}
+	if reloadedPreset.StorageExpiresAt == nil || !reloadedPreset.StorageExpiresAt.Equal(fixed) {
+		t.Fatalf("preset card storage_expires_at was overwritten: %v", reloadedPreset.StorageExpiresAt)
+	}
+}

pkg/database/seed.go

@@ -4,8 +4,9 @@ import (
 	"fmt"
 	"log"
 
-	"gorm.io/gorm"
 	"terminalShop/pkg/models"
+
+	"gorm.io/gorm"
 )
 
 // Seed populates the database with initial data
@@ -25,54 +26,60 @@ func Seed(db *gorm.DB) error {
 		{
 			Name:        "Espresso",
 			RoastType:   "Dark Roast",
+			RoastLevel:  5,
 			Ounces:      2,
 			BeanType:    "Arabica",
-			Price:       350, // $3.50
+			Price:       1800, // $18.00
 			Color:       "#8B4513",
 			Description: "Bold and intense coffee with a rich crema",
 		},
 		{
 			Name:        "Americano",
 			RoastType:   "Medium Roast",
+			RoastLevel:  3,
 			Ounces:      8,
 			BeanType:    "Arabica",
-			Price:       400, // $4.00
+			Price:       2200, // $22.00
 			Color:       "#A0522D",
 			Description: "Smooth and balanced espresso diluted with hot water",
 		},
 		{
 			Name:        "Cappuccino",
 			RoastType:   "Medium Roast",
+			RoastLevel:  3,
 			Ounces:      6,
 			BeanType:    "Arabica",
-			Price:       450, // $4.50
+			Price:       2200, // $22.00
 			Color:       "#C4A574",
 			Description: "Espresso with steamed milk and a thick layer of foam",
 		},
 		{
 			Name:        "Latte",
 			RoastType:   "Medium Roast",
+			RoastLevel:  2,
 			Ounces:      12,
 			BeanType:    "Arabica",
-			Price:       500, // $5.00
+			Price:       2500, // $25.00
 			Color:       "#D2B48C",
 			Description: "Creamy espresso with plenty of steamed milk and a touch of foam",
 		},
 		{
 			Name:        "Mocha",
 			RoastType:   "Dark Roast",
+			RoastLevel:  4,
 			Ounces:      12,
 			BeanType:    "Arabica",
-			Price:       550, // $5.50
+			Price:       3000, // $30.00
 			Color:       "#8B4513",
 			Description: "Chocolate and espresso combined with steamed milk. Sweet and indulgent.",
 		},
 		{
 			Name:        "Macchiato",
 			RoastType:   "Dark Roast",
+			RoastLevel:  4,
 			Ounces:      3,
 			BeanType:    "Robusta Blend",
-			Price:       425, // $4.25
+			Price:       1800, // $18.00
 			Color:       "#DAA520",
 			Description: "Espresso 'marked' with a dollop of foamed milk. Small but mighty, like a tiny caffeinated warrior.",
 		},

pkg/models/card.go

@@ -6,21 +6,25 @@ import (
 	"gorm.io/gorm"
 )
 
+const cardStorageTTL = 180 * 24 * time.Hour
+
 // Card represents a saved payment method linked to a Stripe token.
 // The actual card details live on Stripe's servers — we only store
 // a reference and display info (last 4 digits, brand).
 type Card struct {
-	ID              uint           `gorm:"primaryKey" json:"id"`
-	UserID          uint           `gorm:"not null;index" json:"user_id"`
-	StripePaymentID string         `gorm:"size:255;not null" json:"-"`   // Stripe payment method or token ID
-	Last4           string         `gorm:"size:4;not null" json:"last4"` // Last 4 digits for display
-	Brand           string         `gorm:"size:50" json:"brand"`         // Visa, Mastercard, etc.
-	ExpMonth        int            `gorm:"not null" json:"exp_month"`
-	ExpYear         int            `gorm:"not null" json:"exp_year"`
-	IsDefault       bool           `gorm:"default:false" json:"is_default"` // User's preferred card
-	CreatedAt       time.Time      `json:"created_at"`
-	UpdatedAt       time.Time      `json:"updated_at"`
-	DeletedAt       gorm.DeletedAt `gorm:"index" json:"-"`
+	ID               uint           `gorm:"primaryKey" json:"id"`
+	UserID           uint           `gorm:"not null;index" json:"user_id"`
+	StripePaymentID  string         `gorm:"size:255;not null" json:"-"`   // Stripe payment method or token ID
+	Last4            string         `gorm:"size:4;not null" json:"last4"` // Last 4 digits for display
+	Brand            string         `gorm:"size:50" json:"brand"`         // Visa, Mastercard, etc.
+	ExpMonth         int            `gorm:"not null" json:"exp_month"`
+	ExpYear          int            `gorm:"not null" json:"exp_year"`
+	IsDefault        bool           `gorm:"default:false" json:"is_default"` // User's preferred card
+	CreatedAt        time.Time      `json:"created_at"`
+	UpdatedAt        time.Time      `json:"updated_at"`
+	DeletedAt        gorm.DeletedAt `gorm:"index" json:"-"`
+	LastUsedAt       *time.Time     `json:"last_used_at,omitempty"`
+	StorageExpiresAt *time.Time     `gorm:"index" json:"storage_expires_at,omitempty"`
 
 	// Associations
 	User User `gorm:"foreignKey:UserID" json:"-"`
@@ -30,3 +34,20 @@ type Card struct {
 func (Card) TableName() string {
 	return "cards"
 }
+
+// CardStorageExpiresAt returns the inactivity expiration for a saved card
+func CardStorageExpiresAt(now time.Time) *time.Time {
+	expiresAt := now.Add(cardStorageTTL)
+	return &expiresAt
+}
+
+// InitializeStorageTTL sets the initial retention deadline without marking
+// the card as used for payment
+func (c *Card) InitializeStorageTTL(now time.Time) {
+	c.StorageExpiresAt = CardStorageExpiresAt(now)
+}
+
+// IsStorageExpired reports whether the saved card retention deadline elapsed
+func (c *Card) IsStorageExpired(now time.Time) bool {
+	return c.StorageExpiresAt != nil && !c.StorageExpiresAt.After(now)
+}

pkg/models/card_test.go

@@ -0,0 +1,26 @@
+package models
+
+import (
+	"testing"
+	"time"
+)
+
+func TestCardStorageTTL(t *testing.T) {
+	now := time.Date(2026, 6, 2, 12, 0, 0, 0, time.UTC)
+
+	var card Card
+	card.InitializeStorageTTL(now)
+
+	if card.LastUsedAt != nil {
+		t.Fatalf("InitializeStorageTTL should not mark card as used")
+	}
+	if card.StorageExpiresAt == nil || !card.StorageExpiresAt.Equal(now.Add(cardStorageTTL)) {
+		t.Fatalf("unexpected initial expiration: %v", card.StorageExpiresAt)
+	}
+	if card.IsStorageExpired(now.Add(cardStorageTTL - time.Second)) {
+		t.Fatalf("card expired before ttl elapsed")
+	}
+	if !card.IsStorageExpired(now.Add(cardStorageTTL)) {
+		t.Fatalf("card should expire at ttl boundary")
+	}
+}

pkg/models/coffee.go

@@ -11,6 +11,7 @@ type Coffee struct {
 	ID          uint           `gorm:"primaryKey" json:"id"`
 	Name        string         `gorm:"size:255;not null" json:"name"`
 	RoastType   string         `gorm:"size:100" json:"roast_type"`
+	RoastLevel  int            `json:"roast_level"` // 1-5 roast-intensity
 	Ounces      int            `json:"ounces"`
 	BeanType    string         `gorm:"size:100" json:"bean_type"`
 	Price       int            `gorm:"not null" json:"price"`
@@ -28,10 +29,10 @@ func (Coffee) TableName() string {
 
 // AccountMenuItems
 var AccountMenuItems = []string{
+	"active orders",
 	"order history",
 	"addresses",
 	"cards",
-	"ssh keys",
 	"faq",
 	"about",
 }

pkg/models/doc.go

@@ -0,0 +1,3 @@
+// Package models is the shared vocabulary of the app: coffee, carts, orders,
+// addresses, cards, users, and the other nouns everything passes around.
+package models

pkg/models/order.go

@@ -10,41 +10,76 @@ import (
 type OrderStatus string
 
 const (
-	OrderStatusPending   OrderStatus = "pending"
-	OrderStatusPaid      OrderStatus = "paid"
-	OrderStatusShipped   OrderStatus = "shipped"
-	OrderStatusDelivered OrderStatus = "delivered"
-	OrderStatusCancelled OrderStatus = "cancelled"
-	OrderStatusRefunded  OrderStatus = "refunded"
-	OrderStatusFailed    OrderStatus = "failed"
+	OrderStatusPending        OrderStatus = "pending"
+	OrderStatusRequiresAction OrderStatus = "requires_action"
+	OrderStatusPaid           OrderStatus = "paid"
+	OrderStatusShipped        OrderStatus = "shipped"
+	OrderStatusDelivered      OrderStatus = "delivered"
+	OrderStatusCancelled      OrderStatus = "cancelled"
+	OrderStatusRefunded       OrderStatus = "refunded"
+	OrderStatusFailed         OrderStatus = "failed"
+)
+
+type TrackingStatus string
+
+const (
+	TrackingStatusUnknown    TrackingStatus = ""
+	TrackingStatusPreTransit TrackingStatus = "pre_transit"
+	TrackingStatusTransit    TrackingStatus = "transit"
+	TrackingStatusDelivered  TrackingStatus = "delivered"
+	TrackingStatusReturned   TrackingStatus = "returned"
+	TrackingStatusFailure    TrackingStatus = "failure"
 )
 
 // Order represents a completed purchase.
 type Order struct {
-	ID              uint           `gorm:"primaryKey" json:"id"`
-	UserID          uint           `gorm:"not null;index" json:"user_id"`
-	CardID          uint           `gorm:"not null" json:"card_id"`
-	StripePaymentID string         `gorm:"size:255" json:"-"` // Stripe PaymentIntent ID
-	Status          OrderStatus    `gorm:"size:50;not null;default:'pending'" json:"status"`
-	Subtotal        int            `gorm:"not null" json:"subtotal"`       // Amount in cents
-	ShippingCost    int            `gorm:"default:0" json:"shipping_cost"` // Amount in cents
-	Total           int            `gorm:"not null" json:"total"`          // Amount in cents
-	ShippingName    string         `gorm:"size:255" json:"shipping_name"`
-	ShippingStreet  string         `gorm:"size:255" json:"shipping_street"`
-	ShippingStreet2 string         `gorm:"size:255" json:"shipping_street2"`
-	ShippingCity    string         `gorm:"size:255" json:"shipping_city"`
-	ShippingState   string         `gorm:"size:50" json:"shipping_state"`
-	ShippingZip     string         `gorm:"size:20" json:"shipping_zip"`
-	ShippingCountry string         `gorm:"size:2" json:"shipping_country"`
-	ShippingPhone   string         `gorm:"size:20" json:"shipping_phone"`
-	CreatedAt       time.Time      `json:"created_at"`
-	UpdatedAt       time.Time      `json:"updated_at"`
-	DeletedAt       gorm.DeletedAt `gorm:"index" json:"-"`
+	ID              uint        `gorm:"primaryKey" json:"id"`
+	UserID          uint        `gorm:"not null;index" json:"user_id"`
+	CardID          uint        `gorm:"not null" json:"card_id"`
+	StripePaymentID string      `gorm:"size:255" json:"-"` // Stripe PaymentIntent ID
+	Status          OrderStatus `gorm:"size:50;not null;default:'pending'" json:"status"`
+	Subtotal        int         `gorm:"not null" json:"subtotal"`         // Amount in cents
+	ShippingCost    int         `gorm:"default:0" json:"shipping_cost"`   // Amount in cents
+	Total           int         `gorm:"not null" json:"total"`            // Amount in cents
+	ShippingName    string      `gorm:"size:255" json:"shipping_name"`    // The name of the person the shipment is tied to
+	ShippingStreet  string      `gorm:"size:255" json:"shipping_street"`  // The street address the shipment is tied to
+	ShippingStreet2 string      `gorm:"size:255" json:"shipping_street2"` // The alternate street address the shipment is going to if first is valid for whatever reason
+	ShippingCity    string      `gorm:"size:255" json:"shipping_city"`    // The city the shipment is going to
+	ShippingState   string      `gorm:"size:50" json:"shipping_state"`    // The state the shipment is tied to
+	ShippingZip     string      `gorm:"size:20" json:"shipping_zip"`      // The zip code the order is tied to
+	ShippingCountry string      `gorm:"size:2" json:"shipping_country"`   // The country the shipment is tied to
+	ShippingPhone   string      `gorm:"size:20" json:"shipping_phone"`    // Phone number the shipment is tied to
+
+	// Shipment / tracking - single embedded blob (since its just one warehouse (my house))
+	Carrier                 string         `gorm:"size:100" json:"carrier"`
+	TrackingNumber          string         `gorm:"size:255;index" json:"tracking_number"`
+	TrackingURL             string         `gorm:"size:512" json:"tracking_url"`
+	ShippedAt               *time.Time     `json:"shipped_at"`
+	TrackingStatus          TrackingStatus `gorm:"size:50" json:"tracking_status"`
+	TrackingStatusDetails   string         `gorm:"size:512" json:"tracking_status_details"`
+	TrackingStatusUpdatedAt *time.Time     `json:"tracking_status_updated_at"`
+
+	// Shippo label shit, populated by the PurchaseLabel handler
+	ShippoTransactionID *string `gorm:"size:255;uniqueIndex" json:"-"`
+	LabelURL            string  `gorm:"size:512" json:"-"`
+	LabelCostCents      int     `json:"-"`
+
+	// Slack parent message ts for this order's thread (NULL if Slack notify disabled).
+	SlackThreadTS *string `gorm:"size:64" json:"-"`
+
+	// LastRefundRequestAt timestamps the most recent customer-initiated refund
+	// request for this order. Used to rate-limit repeat submissions.
+	LastRefundRequestAt *time.Time `json:"-"`
+
+	CreatedAt time.Time      `json:"created_at"`
+	UpdatedAt time.Time      `json:"updated_at"`
+	DeletedAt gorm.DeletedAt `gorm:"index" json:"-"` // GORM soft-delete sentinel
 
 	// Associations
-	User  User        `gorm:"foreignKey:UserID" json:"-"`
-	Card  Card        `gorm:"foreignKey:CardID" json:"-"`
-	Items []OrderItem `gorm:"foreignKey:OrderID" json:"items"`
+	User   User         `gorm:"foreignKey:UserID" json:"-"`
+	Card   Card         `gorm:"foreignKey:CardID" json:"-"`
+	Items  []OrderItem  `gorm:"foreignKey:OrderID" json:"items"`
+	Events []OrderEvent `gorm:"foreignKey:OrderID" json:"events,omitempty"`
 }
 
 // TableName specifies the table name for the Order model.
@@ -77,3 +112,41 @@ func (OrderItem) TableName() string {
 func (o *Order) TotalInDollars() float64 {
 	return float64(o.Total) / 100
 }
+
+// IsActive returns whether the order is still active, which is paid but unfulfilled,
+// or shipped but not yet delivered.
+func (o *Order) IsActive() bool {
+	return o.Status == OrderStatusPaid || o.Status == OrderStatusShipped
+}
+
+// RefundRequestReasons is the canonical list of customer-facing refund reasons
+// accepted by both the API and the TUI.
+var RefundRequestReasons = []string{
+	"Wrong item received",
+	"Item damaged in transit",
+	"Item never arrived",
+	"Quality issue",
+	"Other",
+}
+
+// RefundRequestReasonOther is the sentinel reason that requires a free-form message.
+const RefundRequestReasonOther = "Other"
+
+// IsValidRefundReason reports whether r is one of the accepted refund reasons.
+func IsValidRefundReason(r string) bool {
+	for _, reason := range RefundRequestReasons {
+		if reason == r {
+			return true
+		}
+	}
+	return false
+}
+
+// CanRequestRefund reports whether a customer is allowed to request a refund
+// for this order. Paid, shipped, and delivered orders qualify; everything else
+// is either still unpaid or already in a terminal state.
+func (o *Order) CanRequestRefund() bool {
+	return o.Status == OrderStatusPaid ||
+		o.Status == OrderStatusShipped ||
+		o.Status == OrderStatusDelivered
+}

pkg/models/order_display.go

@@ -0,0 +1,100 @@
+package models
+
+// DisplayKind is a ui agnostic color/severity token.
+// The TUI (or any other renderer) maps this to a concrete style
+// the model stays free of UI deps.
+type DisplayKind string
+
+const (
+	DisplayKindNeutral DisplayKind = "neutral" // pending, default
+	DisplayKindAccent  DisplayKind = "accent"  // paid, awaiting fulfillment
+	DisplayKindBrand   DisplayKind = "brand"   // shipped / in transit
+	DisplayKindSuccess DisplayKind = "success" // delivered
+	DisplayKindError   DisplayKind = "error"   // cancelled, failed, refunded
+	DisplayKindWarning DisplayKind = "warning" // delivery issue, returned
+	DisplayKindRefund  DisplayKind = "refund"  // refund requested, awaiting review
+)
+
+// refundPending reports whether the order has an open customer refund request
+// that has not yet been resolved by a terminal status change.
+func (order *Order) refundPending() bool {
+	if order.LastRefundRequestAt == nil {
+		return false
+	}
+	switch order.Status {
+	case OrderStatusRefunded, OrderStatusCancelled, OrderStatusFailed:
+		return false
+	}
+	return true
+}
+
+func (order *Order) DisplayState() string {
+	if order.refundPending() {
+		return "Refund Requested"
+	}
+	switch order.Status {
+	case OrderStatusPending:
+		return "Awaiting payment"
+	case OrderStatusRequiresAction:
+		return "Awaiting authentication"
+	case OrderStatusPaid:
+		if order.TrackingNumber == "" {
+			return "Paid * awaiting label"
+		}
+		// !IMPORTANT
+		// Reachable only if UpdateTracking auto-promote is removed later
+		if order.TrackingStatus == TrackingStatusPreTransit {
+			return "Paid * ready to ship"
+		}
+		return "Paid"
+	case OrderStatusShipped:
+		switch order.TrackingStatus {
+		case TrackingStatusTransit:
+			return "In Transit"
+		case TrackingStatusFailure:
+			return "Delivery Issue"
+		case TrackingStatusReturned:
+			return "Returned to Sender"
+		case TrackingStatusDelivered:
+			// Webhook hasn't promoted Status yet, trust tracking
+			return "Delivered"
+		}
+		return "Label Created"
+	case OrderStatusDelivered:
+		return "Delivered"
+	case OrderStatusCancelled:
+		return "Cancelled"
+	case OrderStatusRefunded:
+		return "Refunded"
+	case OrderStatusFailed:
+		return "Payment failed"
+	}
+	return string(order.Status)
+}
+
+func (order *Order) DisplayKind() DisplayKind {
+	if order.refundPending() {
+		return DisplayKindRefund
+	}
+	switch order.Status {
+	case OrderStatusPending:
+		return DisplayKindNeutral
+	case OrderStatusRequiresAction:
+		return DisplayKindNeutral
+	case OrderStatusPaid:
+		return DisplayKindAccent
+	case OrderStatusShipped:
+		switch order.TrackingStatus {
+		case TrackingStatusFailure, TrackingStatusReturned:
+			return DisplayKindWarning
+		case TrackingStatusDelivered:
+			return DisplayKindSuccess
+		}
+		return DisplayKindBrand
+	case OrderStatusDelivered:
+		return DisplayKindSuccess
+	case OrderStatusCancelled, OrderStatusRefunded, OrderStatusFailed:
+		return DisplayKindError
+	}
+	return DisplayKindNeutral
+}

pkg/models/order_display_test.go

@@ -0,0 +1,46 @@
+package models
+
+import (
+	"testing"
+	"time"
+)
+
+func TestOrderDisplayState(t *testing.T) {
+	now := time.Now()
+	tests := []struct {
+		name  string
+		order Order
+		want  string
+		kind  DisplayKind
+	}{
+		{"pending", Order{Status: OrderStatusPending}, "Awaiting payment", DisplayKindNeutral},
+		{"requires_action", Order{Status: OrderStatusRequiresAction}, "Awaiting authentication", DisplayKindNeutral},
+		{"paid no tracking", Order{Status: OrderStatusPaid}, "Paid * awaiting label", DisplayKindAccent},
+		{"paid with tracking, no event", Order{Status: OrderStatusPaid, TrackingNumber: "12999"}, "Paid", DisplayKindAccent},
+		{"Paid pre-transit", Order{Status: OrderStatusPaid, TrackingNumber: "12999", TrackingStatus: TrackingStatusPreTransit}, "Paid * ready to ship", DisplayKindAccent},
+		{"shipped no tracking event", Order{Status: OrderStatusShipped}, "Label Created", DisplayKindBrand},
+		{"shipped pre-transit", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusPreTransit}, "Label Created", DisplayKindBrand},
+		{"shipped in transit", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusTransit}, "In Transit", DisplayKindBrand},
+		{"shipped failure", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusFailure}, "Delivery Issue", DisplayKindWarning},
+		{"shipped returned", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusReturned}, "Returned to Sender", DisplayKindWarning},
+		{"shipped tracking-delivered (webhook lag)", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusDelivered}, "Delivered", DisplayKindSuccess},
+		{"delivered", Order{Status: OrderStatusDelivered}, "Delivered", DisplayKindSuccess},
+		{"cancelled", Order{Status: OrderStatusCancelled}, "Cancelled", DisplayKindError},
+		{"refunded", Order{Status: OrderStatusRefunded}, "Refunded", DisplayKindError},
+		{"failed", Order{Status: OrderStatusFailed}, "Payment failed", DisplayKindError},
+		{"paid with open refund request", Order{Status: OrderStatusPaid, LastRefundRequestAt: &now}, "Refund Requested", DisplayKindRefund},
+		{"delivered with open refund request", Order{Status: OrderStatusDelivered, LastRefundRequestAt: &now}, "Refund Requested", DisplayKindRefund},
+		{"refunded order ignores prior request", Order{Status: OrderStatusRefunded, LastRefundRequestAt: &now}, "Refunded", DisplayKindError},
+		{"cancelled order ignores prior request", Order{Status: OrderStatusCancelled, LastRefundRequestAt: &now}, "Cancelled", DisplayKindError},
+	}
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			if got := tc.order.DisplayState(); got != tc.want {
+				t.Errorf("DisplayState() = %q, want %q", got, tc.want)
+			}
+			if got := tc.order.DisplayKind(); got != tc.kind {
+				t.Errorf("DisplayKind() = %q, want %q", got, tc.kind)
+			}
+		})
+	}
+}

pkg/models/order_event.go

@@ -0,0 +1,63 @@
+package models
+
+import (
+	"encoding/json"
+	"time"
+)
+
+type OrderEvent struct {
+	ID        uint      `gorm:"primaryKey" json:"id"`
+	OrderID   uint      `gorm:"not null;index" json:"order_id"`
+	Type      string    `gorm:"size:100;not null;index" json:"type"`
+	Payload   string    `gorm:"type:text" json:"payload"`
+	Actor     string    `gorm:"size:255" json:"actor"`
+	CreatedAt time.Time `json:"created_at"`
+}
+
+func (OrderEvent) TableName() string {
+	return "order_events"
+}
+
+func (e *OrderEvent) PayloadMap() map[string]any {
+	if e.Payload == "" {
+		return nil
+	}
+	var m map[string]any
+	if err := json.Unmarshal([]byte(e.Payload), &m); err != nil {
+		return nil
+	}
+	return m
+}
+
+func (e *OrderEvent) DisplayLabel() (string, bool) {
+	switch e.Type {
+	case "order_paid":
+		return "Paid", true
+	case "label_purchased":
+		return "Label created", true
+	case "order_delivered":
+		return "Delivered", true
+	case "order_refunded":
+		return "Refunded", true
+	case "order_failed":
+		return "Payment failed", true
+	case "tracking_updated":
+		status, _ := e.PayloadMap()["status"].(string)
+		return trackingLabel(status)
+	}
+	return "", false
+}
+
+func trackingLabel(status string) (string, bool) {
+	switch status {
+	case "transit":
+		return "In transit", true
+	case "failure":
+		return "Delivery issue", true
+	case "returned":
+		return "Returned to sender", true
+	case "pre_transit":
+		return "Label scanned by carrier", true
+	}
+	return "", false
+}

pkg/models/pay_redirect.go

@@ -0,0 +1,23 @@
+package models
+
+import "time"
+
+// PayRedirect maps a short token to a stripe hosted url with a TTL.
+// survives api restarts so a customer mid-3Ds authentication still
+// lands on the bank-hosted challenge page after a deploy or crash
+type PayRedirect struct {
+	Token     string    `gorm:"primaryKey;size:64" json:"token"`
+	URL       string    `gorm:"type:text;not null" json:"url"`
+	Purpose   string    `gorm:"size:32;not null" json:"purpose"`
+	CreatedAt time.Time `json:"created_at"`
+	ExpiresAt time.Time `gorm:"index" json:"expires_at"`
+}
+
+const (
+	RedirectPurposeCheckout3DS = "checkout_3ds"
+	RedirectPurposeAddCard     = "add_card"
+)
+
+func (PayRedirect) TableName() string {
+	return "pay_redirects"
+}

pkg/notify/slack.go

@@ -0,0 +1,327 @@
+// Package notify provides a simple interface to send notifications to Slack.
+package notify
+
+import (
+	"bytes"
+	"encoding/json"
+	"fmt"
+	"log/slog"
+	"net/http"
+	"os"
+	"strings"
+	"time"
+
+	"terminalShop/pkg/database"
+	"terminalShop/pkg/models"
+)
+
+// slack client
+var slackClient = &http.Client{Timeout: 5 * time.Second}
+
+// dollars converts cents to dollars
+func dollars(cents int) string {
+	return fmt.Sprintf("$%.2f", float64(cents)/100)
+}
+
+// postSlackMessage POSTs to chat.postMessage and returns (ts, ok). Logs on failure.
+func postSlackMessage(token string, payload map[string]any) (string, bool) {
+	body, _ := json.Marshal(payload)
+	req, _ := http.NewRequest(http.MethodPost, "https://slack.com/api/chat.postMessage", bytes.NewReader(body))
+	req.Header.Set("Content-Type", "application/json; charset=utf-8")
+	req.Header.Set("Authorization", "Bearer "+token)
+
+	resp, err := slackClient.Do(req)
+	if err != nil {
+		slog.Warn("slack post failed", "error", err)
+		return "", false
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	var parsed struct {
+		Ok    bool   `json:"ok"`
+		TS    string `json:"ts"`
+		Error string `json:"error"`
+	}
+	_ = json.NewDecoder(resp.Body).Decode(&parsed)
+	if !parsed.Ok {
+		slog.Warn("slack post non-ok", "error", parsed.Error)
+		return "", false
+	}
+	return parsed.TS, true
+}
+
+func pinMessage(token, channel, ts string) bool {
+	return slackPinCall(token, "https://slack.com/api/pins.add", channel, ts, "already_pinned")
+}
+
+func unpinMessage(token, channel, ts string) bool {
+	return slackPinCall(token, "https://slack.com/api/pins.remove", channel, ts, "no_pin")
+}
+
+func slackPinCall(token, endpoint, channel, ts, benignErr string) bool {
+	body, _ := json.Marshal(map[string]any{"channel": channel, "timestamp": ts})
+	req, _ := http.NewRequest(http.MethodPost, endpoint, bytes.NewReader(body))
+	req.Header.Set("Content-Type", "application/json; charset=utf-8")
+	req.Header.Set("Authorization", "Bearer "+token)
+
+	resp, err := slackClient.Do(req)
+	if err != nil {
+		slog.Warn("slack pin call failed", "endpoint", endpoint, "error", err)
+		return false
+	}
+	defer func() { _ = resp.Body.Close() }()
+
+	var parsed struct {
+		Ok    bool   `json:"ok"`
+		Error string `json:"error"`
+	}
+	_ = json.NewDecoder(resp.Body).Decode(&parsed)
+	if !parsed.Ok && parsed.Error != benignErr {
+		slog.Warn("slack pin call non-ok", "endpoint", endpoint, "error", parsed.Error)
+		return false
+	}
+	return true
+}
+
+func buildReceiptBlocks(order *models.Order) []map[string]any {
+	blocks := []map[string]any{
+		{"type": "divider"},
+	}
+	for _, item := range order.Items {
+		line := fmt.Sprintf("*%s* × %d\n%s", item.Name, item.Quantity, dollars(item.Price*item.Quantity))
+		blocks = append(blocks, map[string]any{
+			"type": "section",
+			"text": map[string]any{"type": "mrkdwn", "text": line},
+		})
+	}
+	blocks = append(blocks,
+		map[string]any{"type": "divider"},
+		map[string]any{
+			"type": "section",
+			"fields": []map[string]any{
+				{"type": "mrkdwn", "text": "*Subtotal:*\n" + dollars(order.Subtotal)},
+				{"type": "mrkdwn", "text": "*Shipping:*\n" + dollars(order.ShippingCost)},
+				{"type": "mrkdwn", "text": "*Total:*\n" + dollars(order.Total)},
+			},
+		},
+		map[string]any{
+			"type": "section",
+			"text": map[string]any{
+				"type": "mrkdwn",
+				"text": fmt.Sprintf(":package: *Ship to:*\n%s\n%s\n%s, %s %s",
+					order.ShippingName,
+					order.ShippingStreet,
+					order.ShippingCity,
+					order.ShippingZip,
+					order.ShippingCountry,
+				),
+			},
+		},
+		map[string]any{
+			"type": "actions",
+			"elements": []map[string]any{
+				{
+					"type":      "button",
+					"text":      map[string]any{"type": "plain_text", "text": "Buy Label", "emoji": true},
+					"value":     fmt.Sprintf("%d", order.ID),
+					"action_id": "buy_label",
+					"style":     "primary",
+				},
+			},
+		},
+	)
+	return blocks
+}
+
+// SlackOrderPaid posts a compact parent message ("Order #N paid - $X.XX") to
+// the orders channel, persists the resulting ts onto the order, and posts the
+// full receipt as the first thread reply. All subsequent order events
+// (label-buy, tracking updates) should be posted as further thread replies
+// via SlackPostToOrderThread. No-op if SLACK_BOT_TOKEN or SLACK_CHANNEL unset.
+func SlackOrderPaid(order *models.Order) {
+	token := os.Getenv("SLACK_BOT_TOKEN")
+	channel := os.Getenv("SLACK_CHANNEL")
+	if token == "" || channel == "" {
+		return
+	}
+
+	parentText := fmt.Sprintf(":coffee: Order #%d paid - %s", order.ID, dollars(order.Total))
+	ts, ok := postSlackMessage(token, map[string]any{
+		"channel": channel,
+		"text":    parentText,
+	})
+	if !ok {
+		return
+	}
+
+	if err := database.GetDB().Model(&models.Order{}).Where("id = ?", order.ID).Update("slack_thread_ts", ts).Error; err != nil {
+		slog.Warn("failed to save slack thread ts", "order_id", order.ID, "error", err)
+	}
+
+	pinMessage(token, channel, ts)
+
+	_, _ = postSlackMessage(token, map[string]any{
+		"channel":   channel,
+		"thread_ts": ts,
+		"text":      parentText,
+		"blocks":    buildReceiptBlocks(order),
+	})
+}
+
+func SlackUnpinOrder(orderID uint) {
+	token := os.Getenv("SLACK_BOT_TOKEN")
+	channel := os.Getenv("SLACK_CHANNEL")
+	if token == "" || channel == "" {
+		return
+	}
+
+	var order models.Order
+	if err := database.GetDB().Select("id", "slack_thread_ts").Where("id = ?", orderID).First(&order).Error; err != nil {
+		slog.Warn("failed to look up order for unpin", "order_id", orderID, "error", err)
+		return
+	}
+	if order.SlackThreadTS == nil || *order.SlackThreadTS == "" {
+		return
+	}
+
+	unpinMessage(token, channel, *order.SlackThreadTS)
+}
+
+// SlackPostToOrderThread posts a plain-text reply inside the order's thread.
+// It looks up the thread ts from the database and returns an error when the
+// reply cannot be posted.
+func SlackPostToOrderThread(orderID uint, text string) error {
+	return slackPostToOrderThread(orderID, text, false)
+}
+
+// SlackPostToOrderThreadBroadcast posts a thread reply that is also surfaced
+// to the channel (reply_broadcast=true) so channel members get a normal
+// notification. Use for messages that need immediate operator attention.
+func SlackPostToOrderThreadBroadcast(orderID uint, text string) error {
+	return slackPostToOrderThread(orderID, text, true)
+}
+
+func slackPostToOrderThread(orderID uint, text string, broadcast bool) error {
+	token := os.Getenv("SLACK_BOT_TOKEN")
+	channel := os.Getenv("SLACK_CHANNEL")
+	if token == "" || channel == "" {
+		return fmt.Errorf("slack is not configured")
+	}
+
+	var order models.Order
+	if err := database.GetDB().Select("id", "slack_thread_ts").Where("id = ?", orderID).First(&order).Error; err != nil {
+		slog.Warn("failed to look up order for thread post", "order_id", orderID, "error", err)
+		return fmt.Errorf("failed to look up order thread: %w", err)
+	}
+	if order.SlackThreadTS == nil || *order.SlackThreadTS == "" {
+		return fmt.Errorf("order has no slack thread")
+	}
+
+	payload := map[string]any{
+		"channel":   channel,
+		"thread_ts": *order.SlackThreadTS,
+		"text":      text,
+	}
+	if broadcast {
+		payload["reply_broadcast"] = true
+	}
+
+	if _, ok := postSlackMessage(token, payload); !ok {
+		slog.Warn("failed to post slack thread reply", "order_id", orderID)
+		return fmt.Errorf("failed to post slack thread reply")
+	}
+	return nil
+}
+
+func SlackPostLabelPurchased(orderID uint, labelURL string, costCents int) {
+	token := os.Getenv("SLACK_BOT_TOKEN")
+	channel := os.Getenv("SLACK_CHANNEL")
+	if token == "" || channel == "" {
+		return
+	}
+
+	var order models.Order
+	if err := database.GetDB().
+		Select("id", "carrier", "tracking_number", "tracking_url", "slack_thread_ts").
+		Where("id = ?", orderID).First(&order).Error; err != nil {
+		slog.Warn("failed to look up order for label-purchased slack post", "order_id", orderID, "error", err)
+		return
+	}
+	if order.SlackThreadTS == nil || *order.SlackThreadTS == "" {
+		return
+	}
+
+	headLine := fmt.Sprintf(":white_check_mark: Labeled - %s `%s` (%s). <%s|Download label PDF>", order.Carrier, order.TrackingNumber, dollars(costCents), labelURL)
+
+	blocks := []map[string]any{
+		{
+			"type": "section",
+			"text": map[string]any{"type": "mrkdwn", "text": headLine},
+		},
+	}
+
+	if strings.EqualFold(order.Carrier, "BRING") {
+		blocks = append(blocks, markStatusActionBlock(order.ID))
+	}
+
+	_, _ = postSlackMessage(token, map[string]any{
+		"channel":   channel,
+		"thread_ts": *order.SlackThreadTS,
+		"text":      headLine,
+		"blocks":    blocks,
+	})
+}
+
+func markStatusActionBlock(orderID uint) map[string]any {
+	id := fmt.Sprintf("%d", orderID)
+	return map[string]any{
+		"type": "actions",
+		"elements": []map[string]any{
+			{"type": "button", "text": map[string]any{"type": "plain_text", "text": "Mark Pre-Transit", "emoji": true}, "value": id, "action_id": "mark_pre_transit"},
+			{"type": "button", "text": map[string]any{"type": "plain_text", "text": "Mark In Transit", "emoji": true}, "value": id, "action_id": "mark_in_transit", "style": "primary"},
+			{"type": "button", "text": map[string]any{"type": "plain_text", "text": "Mark Delivered", "emoji": true}, "value": id, "action_id": "mark_delivered"},
+		},
+	}
+}
+
+func SlackUnshippedReminder(orders []models.Order) {
+	token := os.Getenv("SLACK_BOT_TOKEN")
+	channel := os.Getenv("SLACK_CHANNEL")
+	if token == "" || channel == "" || len(orders) == 0 {
+		return
+	}
+
+	workspace := os.Getenv("SLACK_WORKSPACE_SUBDOMAIN")
+
+	lines := []string{fmt.Sprintf(":hourglass_flowing_sand: %d order(s) awaiting label", len(orders))}
+	for _, order := range orders {
+		lines = append(lines, " "+unshippedOrderLine(order, channel, workspace))
+	}
+
+	_, _ = postSlackMessage(token, map[string]any{
+		"channel": channel,
+		"text":    strings.Join(lines, "\n"),
+	})
+}
+
+func unshippedOrderLine(order models.Order, channel, workspace string) string {
+	age := time.Since(order.CreatedAt).Round(time.Hour)
+	location := order.ShippingCountry
+	if order.ShippingCity != "" {
+		location = order.ShippingCity + ", " + order.ShippingCountry
+	}
+
+	label := fmt.Sprintf("Order #%d", order.ID)
+	if order.SlackThreadTS != nil && *order.SlackThreadTS != "" && workspace != "" {
+		ts := strings.ReplaceAll(*order.SlackThreadTS, ".", "")
+		permalink := fmt.Sprintf("https://%s.slack.com/archives/%s/p%s", workspace, channel, ts)
+		label = fmt.Sprintf("<%s|Order #%d>", permalink, order.ID)
+	}
+
+	tag := ""
+	if order.ShippingCountry == "NO" {
+		tag = " _(NO * Bring blocked)_"
+	}
+
+	return fmt.Sprintf("%s * %s old * %s * %s%s", label, age, dollars(order.Total), location, tag)
+}

pkg/observability/doc.go

@@ -0,0 +1,3 @@
+// Package observability sets up tracing and structured logs so that when
+// something breaks at 3am you stand a chance of figuring out why.
+package observability

pkg/observability/logger.go

@@ -0,0 +1,62 @@
+package observability
+
+import (
+	"context"
+	"log"
+	"log/slog"
+	"os"
+	"strings"
+
+	"terminalShop/api/middleware"
+)
+
+// countingHandler wraps a slog.Handler and increments the log_messages_total
+// counter for every record before delegating to the inner handler. This is
+// what gives the dashboard a per-level log rate without forcing call sites
+// to thread metrics manually.
+type countingHandler struct {
+	inner slog.Handler
+}
+
+func (h *countingHandler) Enabled(ctx context.Context, l slog.Level) bool {
+	return h.inner.Enabled(ctx, l)
+}
+
+func (h *countingHandler) Handle(ctx context.Context, r slog.Record) error {
+	middleware.RecordLogLevel(strings.ToLower(r.Level.String()))
+	return h.inner.Handle(ctx, r)
+}
+
+func (h *countingHandler) WithAttrs(attrs []slog.Attr) slog.Handler {
+	return &countingHandler{inner: h.inner.WithAttrs(attrs)}
+}
+
+func (h *countingHandler) WithGroup(name string) slog.Handler {
+	return &countingHandler{inner: h.inner.WithGroup(name)}
+}
+
+// InitLogger installs a slog-based default logger with a level-counting wrapper
+// and bridges the stdlib `log` package through slog so existing log.Printf
+// calls are also counted (as INFO).
+func InitLogger() {
+	level := slog.LevelInfo
+	if env := strings.ToLower(os.Getenv("LOG_LEVEL")); env != "" {
+		switch env {
+		case "debug":
+			level = slog.LevelDebug
+		case "warn", "warning":
+			level = slog.LevelWarn
+		case "error":
+			level = slog.LevelError
+		}
+	}
+
+	base := slog.NewJSONHandler(os.Stdout, &slog.HandlerOptions{Level: level})
+	handler := &countingHandler{inner: base}
+	slog.SetDefault(slog.New(handler))
+
+	// Route the stdlib log package through slog at INFO so legacy log.Printf
+	// calls show up in structured output and bump the counter.
+	slog.SetLogLoggerLevel(slog.LevelInfo)
+	log.SetFlags(0)
+}

pkg/observability/tracing.go

@@ -0,0 +1,32 @@
+package observability
+
+import (
+	"context"
+	"time"
+
+	"go.opentelemetry.io/otel"
+	"go.opentelemetry.io/otel/exporters/otlp/otlptrace/otlptracehttp"
+	"go.opentelemetry.io/otel/propagation"
+	"go.opentelemetry.io/otel/sdk/resource"
+	sdktrace "go.opentelemetry.io/otel/sdk/trace"
+
+	semconv "go.opentelemetry.io/otel/semconv/v1.26.0"
+)
+
+func InitTracing(ctx context.Context, serviceName, endpoint string) (func(context.Context) error, error) {
+	exp, err := otlptracehttp.New(ctx, otlptracehttp.WithEndpoint(endpoint), otlptracehttp.WithInsecure())
+	if err != nil {
+		return nil, err
+	}
+
+	res, err := resource.New(ctx, resource.WithAttributes(semconv.ServiceName(serviceName)))
+	if err != nil {
+		return nil, err
+	}
+
+	tp := sdktrace.NewTracerProvider(sdktrace.WithBatcher(exp, sdktrace.WithBatchTimeout(5*time.Second)), sdktrace.WithResource(res))
+
+	otel.SetTracerProvider(tp)
+	otel.SetTextMapPropagator(propagation.TraceContext{})
+	return tp.Shutdown, nil
+}

pkg/shipping/doc.go

@@ -0,0 +1,3 @@
+// Package shipping holds the plain shipping types that the rest of the app
+// passes back and forth.
+package shipping

pkg/shipping/types.go

@@ -0,0 +1,12 @@
+package shipping
+
+type LabelResult struct {
+	TransactionID  string
+	RateID         string
+	Carrier        string
+	ServiceLevel   string
+	TrackingNumber string
+	TrackingURL    string
+	LabelURL       string
+	CostCents      int
+}

pkg/shippo/doc.go

@@ -0,0 +1,2 @@
+// Package shippo talks to the Shippo API for shipping rates and labels.
+package shippo

pkg/shippo/shippo.go

@@ -2,15 +2,27 @@ package shippo
 
 import (
 	"bytes"
+	"context"
 	"encoding/json"
 	"fmt"
 	"io"
 	"net/http"
+	"os"
+	"sort"
+	"strconv"
+	"terminalShop/pkg/shipping"
 	"time"
+
+	"go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp"
 )
 
 const baseURL = "https://api.goshippo.com"
 
+const (
+	labelPollInterval = 1 * time.Second
+	labelPollTimeout  = 30 * time.Second
+)
+
 // Client handles communication with the Shippo API.
 type Client struct {
 	apiKey     string
@@ -22,11 +34,325 @@ func NewClient(apiKey string) *Client {
 	return &Client{
 		apiKey: apiKey,
 		httpClient: &http.Client{
-			Timeout: 10 * time.Second,
+			Timeout:   10 * time.Second,
+			Transport: otelhttp.NewTransport(http.DefaultTransport),
 		},
 	}
 }
 
+type Parcel struct {
+	LengthCm float64
+	WidthCm  float64
+	HeightCm float64
+	WeightKg float64
+}
+
+type LineItem struct {
+	Title    string
+	Quantity int
+	WeightKg float64
+}
+
+type shipmentRate struct {
+	ObjectID     string `json:"object_id"`
+	Amount       string `json:"amount"`
+	Currency     string `json:"currency"`
+	Provider     string `json:"provider"`
+	ServiceLevel struct {
+		Name string `json:"name"`
+	} `json:"servicelevel"`
+}
+
+type shipmentResponse struct {
+	Status string         `json:"status"`
+	Rates  []shipmentRate `json:"rates"`
+}
+
+type shippoOrderResponse struct {
+	ObjectID string `json:"object_id"`
+}
+
+type transactionResponse struct {
+	ObjectID       string `json:"object_id"`
+	Status         string `json:"status"`
+	ObjectState    string `json:"object_state"`
+	TrackingNumber string `json:"tracking_number"`
+	TrackingURL    string `json:"tracking_url_provider"`
+	LabelURL       string `json:"label_url"`
+	Rate           string `json:"rate"`
+	Messages       []struct {
+		Text string `json:"text"`
+	} `json:"messages"`
+}
+
+func (c *Client) CreateLabel(ctx context.Context, to Address, email string, items []LineItem) (*shipping.LabelResult, error) {
+	from := fromAddress()
+	if from.Street1 == "" {
+		return nil, fmt.Errorf("SHIP_FROM_STREET1 not configured")
+	}
+
+	totalKg := 0.0
+	for _, it := range items {
+		totalKg += float64(it.Quantity) * it.WeightKg
+	}
+	if totalKg <= 0 {
+		return nil, fmt.Errorf("order has zero shipping weight")
+	}
+
+	parcel := Parcel{LengthCm: 30, WidthCm: 30, HeightCm: 30, WeightKg: totalKg}
+
+	rate, err := c.createShipmentForRates(ctx, from, to, parcel)
+	if err != nil {
+		return nil, fmt.Errorf("get rates: %w", err)
+	}
+
+	shippoOrderID, err := c.createShippoOrder(ctx, to, email, items, totalKg)
+	if err != nil {
+		return nil, fmt.Errorf("create shippo order: %w", err)
+	}
+
+	tx, err := c.buyLabel(ctx, rate.ObjectID, shippoOrderID)
+	if err != nil {
+		return nil, fmt.Errorf("buy label: %w", err)
+	}
+
+	final, err := c.pollTransaction(ctx, tx.ObjectID)
+	if err != nil {
+		return nil, fmt.Errorf("poll transaction: %w", err)
+	}
+
+	costCents := parseAmountCents(rate.Amount)
+
+	return &shipping.LabelResult{
+		TransactionID:  final.ObjectID,
+		RateID:         rate.ObjectID,
+		Carrier:        rate.Provider,
+		ServiceLevel:   rate.ServiceLevel.Name,
+		TrackingNumber: final.TrackingNumber,
+		TrackingURL:    final.TrackingURL,
+		LabelURL:       final.LabelURL,
+		CostCents:      costCents,
+	}, nil
+}
+
+func (c *Client) createShipmentForRates(ctx context.Context, from, to Address, parcel Parcel) (*shipmentRate, error) {
+	payload := map[string]any{
+		"address_from": addrPayload(from),
+		"address_to":   addrPayload(to),
+		"parcels": []map[string]any{{
+			"length":        parcel.LengthCm,
+			"width":         parcel.WidthCm,
+			"height":        parcel.HeightCm,
+			"distance_unit": "cm",
+			"weight":        parcel.WeightKg,
+			"mass_unit":     "kg",
+		}},
+		"async": false,
+		"extra": map[string]any{"bypass_address_validation": true},
+	}
+
+	var resp shipmentResponse
+	if err := c.doJSON(ctx, "POST", "/shipments", payload, &resp); err != nil {
+		return nil, err
+	}
+	if resp.Status != "SUCCESS" || len(resp.Rates) == 0 {
+		return nil, fmt.Errorf("shippo returned no rates (status=%s)", resp.Status)
+	}
+
+	filtered := resp.Rates[:0:0]
+	for _, r := range resp.Rates {
+		if r.Provider == "USPS" {
+			filtered = append(filtered, r)
+		}
+	}
+	if len(filtered) == 0 {
+		return nil, fmt.Errorf("no USPS rates available for this route")
+	}
+	resp.Rates = filtered
+
+	sort.Slice(resp.Rates, func(i, j int) bool {
+		ai, _ := strconv.ParseFloat(resp.Rates[i].Amount, 64)
+		aj, _ := strconv.ParseFloat(resp.Rates[j].Amount, 64)
+		return ai < aj
+	})
+	r := resp.Rates[0]
+	return &r, nil
+}
+
+func (c *Client) createShippoOrder(ctx context.Context, to Address, email string, items []LineItem, totalKg float64) (string, error) {
+	lines := make([]map[string]any, 0, len(items))
+	for _, item := range items {
+		lines = append(lines, map[string]any{
+			"quantity":    item.Quantity,
+			"title":       item.Title,
+			"weight":      roundN(item.WeightKg, 4),
+			"weight_unit": "kg",
+		})
+	}
+	toPayload := addrPayload(to)
+	if email != "" {
+		toPayload["email"] = email
+	}
+	payload := map[string]any{
+		"to_address":  toPayload,
+		"line_items":  lines,
+		"placed_at":   time.Now().Format(time.RFC3339),
+		"weight":      roundN(totalKg, 2),
+		"weight_unit": "kg",
+	}
+	var resp shippoOrderResponse
+	if err := c.doJSON(ctx, "POST", "/v1/orders", payload, &resp); err != nil {
+		return "", err
+	}
+	if resp.ObjectID == "" {
+		return "", fmt.Errorf("shippo order returned no object_id")
+	}
+	return resp.ObjectID, nil
+}
+
+func (c *Client) buyLabel(ctx context.Context, rateID, shippoOrderID string) (*transactionResponse, error) {
+	payload := map[string]any{
+		"rate":  rateID,
+		"order": shippoOrderID,
+		"async": true,
+	}
+	var resp transactionResponse
+	if err := c.doJSON(ctx, "POST", "/v1/transactions", payload, &resp); err != nil {
+		return nil, err
+	}
+	if resp.ObjectState == "INVALID" {
+		return nil, fmt.Errorf("transaction invalid: %s", firstMessage(resp.Messages))
+	}
+	return &resp, nil
+}
+
+func (c *Client) pollTransaction(ctx context.Context, txID string) (*transactionResponse, error) {
+	deadLine := time.Now().Add(labelPollTimeout)
+	for {
+		var resp transactionResponse
+		if err := c.doJSON(ctx, "GET", "/transactions/"+txID, nil, &resp); err != nil {
+			return nil, err
+		}
+		switch resp.Status {
+		case "SUCCESS":
+			return &resp, nil
+		case "ERROR":
+			return nil, fmt.Errorf("shippo transaction error: %s", firstMessage(resp.Messages))
+		}
+		if time.Now().After(deadLine) {
+			return nil, fmt.Errorf("timed out waiting for label (last status=%s)", resp.Status)
+		}
+		select {
+		case <-ctx.Done():
+			return nil, ctx.Err()
+		case <-time.After(labelPollInterval):
+		}
+	}
+}
+
+func (c *Client) doJSON(ctx context.Context, method, path string, body any, out any) error {
+	var rdr io.Reader
+	if body != nil {
+		b, err := json.Marshal(body)
+		if err != nil {
+			return fmt.Errorf("marshal: %w", err)
+		}
+		rdr = bytes.NewReader(b)
+	}
+	req, err := http.NewRequestWithContext(ctx, method, baseURL+path, rdr)
+	if err != nil {
+		return fmt.Errorf("new request: %w", err)
+	}
+	req.Header.Set("Content-Type", "application/json")
+	req.Header.Set("Authorization", "ShippoToken "+c.apiKey)
+
+	resp, err := c.httpClient.Do(req)
+	if err != nil {
+		return fmt.Errorf("request: %w", err)
+	}
+	defer func() { _ = resp.Body.Close() }()
+	respBody, err := io.ReadAll(resp.Body)
+	if err != nil {
+		return fmt.Errorf("read response: %w", err)
+	}
+	if resp.StatusCode < 200 || resp.StatusCode >= 300 {
+		return fmt.Errorf("shippo %s %s -> %d: %s", method, path, resp.StatusCode, string(respBody))
+	}
+	if out != nil {
+		if err := json.Unmarshal(respBody, out); err != nil {
+			return fmt.Errorf("parse reponse: %w", err)
+		}
+	}
+	return nil
+}
+
+func addrPayload(a Address) map[string]any {
+	m := map[string]any{
+		"name":    a.Name,
+		"street1": a.Street1,
+		"city":    a.City,
+		"country": a.Country,
+		"zip":     a.Zip,
+	}
+	if a.Street2 != "" {
+		m["street2"] = a.Street2
+	}
+	if a.State != "" {
+		m["state"] = a.State
+	}
+	if a.Phone != "" {
+		m["phone"] = a.Phone
+	}
+	if a.Email != "" {
+		m["email"] = a.Email
+	}
+	return m
+}
+
+// roundN rounds to n decimal places. Shippo's /v1/orders rejects >2 decimals
+// on parcel weight and >4 on line-item weight.
+func roundN(v float64, n int) float64 {
+	pow := 1.0
+	for i := 0; i < n; i++ {
+		pow *= 10
+	}
+	if v >= 0 {
+		return float64(int64(v*pow+0.5)) / pow
+	}
+	return float64(int64(v*pow-0.5)) / pow
+}
+
+func parseAmountCents(s string) int {
+	f, err := strconv.ParseFloat(s, 64)
+	if err != nil {
+		return 0
+	}
+	return int(f * 100)
+}
+
+func firstMessage(msgs []struct {
+	Text string `json:"text"`
+}) string {
+	if len(msgs) == 0 {
+		return "no detail"
+	}
+	return msgs[0].Text
+}
+
+func fromAddress() Address {
+	return Address{
+		Name:    os.Getenv("SHIP_FROM_NAME"),
+		Street1: os.Getenv("SHIP_FROM_STREET1"),
+		Street2: os.Getenv("SHIP_FROM_STREET2"),
+		City:    os.Getenv("SHIP_FROM_CITY"),
+		State:   os.Getenv("SHIP_FROM_STATE"),
+		Country: os.Getenv("SHIP_FROM_COUNTRY"),
+		Zip:     os.Getenv("SHIP_FROM_ZIP"),
+		Phone:   os.Getenv("SHIP_FROM_PHONE"),
+		Email:   os.Getenv("SHIP_FROM_EMAIL"),
+	}
+}
+
 // Address represents a shipping address for validation.
 type Address struct {
 	Name    string `json:"name"`
@@ -37,6 +363,7 @@ type Address struct {
 	Country string `json:"country"`
 	Zip     string `json:"zip"`
 	Phone   string `json:"phone,omitempty"`
+	Email   string `json:"email,omitempty"`
 }
 
 // addressRequest is the payload sent to Shippo's address validation endpoint.
@@ -75,7 +402,7 @@ type addressResponse struct {
 
 // ValidateAddress sends an address to Shippo for validation.
 // Returns the normalized/corrected address if valid, or an error if invalid.
-func (c *Client) ValidateAddress(addr Address) (*Address, error) {
+func (c *Client) ValidateAddress(ctx context.Context, addr Address) (*Address, error) {
 	reqBody := addressRequest{
 		Name:     addr.Name,
 		Street1:  addr.Street1,
@@ -93,7 +420,7 @@ func (c *Client) ValidateAddress(addr Address) (*Address, error) {
 		return nil, fmt.Errorf("failed to marshal address: %w", err)
 	}
 
-	req, err := http.NewRequest("POST", baseURL+"/v1/addresses", bytes.NewReader(body))
+	req, err := http.NewRequestWithContext(ctx, "POST", baseURL+"/v1/addresses", bytes.NewReader(body))
 	if err != nil {
 		return nil, fmt.Errorf("failed to create request: %w", err)
 	}
@@ -105,7 +432,7 @@ func (c *Client) ValidateAddress(addr Address) (*Address, error) {
 	if err != nil {
 		return nil, fmt.Errorf("shippo request failed: %w", err)
 	}
-	defer resp.Body.Close()
+	defer func() { _ = resp.Body.Close() }()
 
 	respBody, err := io.ReadAll(resp.Body)
 	if err != nil {

pkg/stripeclient/doc.go

@@ -0,0 +1,3 @@
+// Package stripeclient wires up the Stripe SDK once at startup (with tracing
+// baked in) so everyone else can just make calls.
+package stripeclient

pkg/stripeclient/init.go

@@ -0,0 +1,22 @@
+package stripeclient
+
+import (
+	"net/http"
+	"time"
+
+	"github.com/stripe/stripe-go/v78"
+	"go.opentelemetry.io/contrib/instrumentation/net/http/otelhttp"
+)
+
+// InitOTel wires the Stripe SDK to use an HTTP client whose transport emits
+// OpenTelemetry client spans. Call once at startup, after tracing is initialized.
+func InitOTel() {
+	httpClient := &http.Client{
+		Timeout:   80 * time.Second,
+		Transport: otelhttp.NewTransport(http.DefaultTransport),
+	}
+	backends := stripe.NewBackends(httpClient)
+	stripe.SetBackend(stripe.APIBackend, backends.API)
+	stripe.SetBackend(stripe.UploadsBackend, backends.Uploads)
+	stripe.SetBackend(stripe.ConnectBackend, backends.Connect)
+}

pkg/tui/account.go

@@ -1,460 +1,268 @@
 package tui
 
 import (
-	"fmt"
 	"strings"
 
-	tea "github.com/charmbracelet/bubbletea"
-	"github.com/charmbracelet/lipgloss"
+	"charm.land/bubbles/v2/viewport"
+	tea "charm.land/bubbletea/v2"
+	"charm.land/lipgloss/v2"
 
 	"terminalShop/pkg/models"
 )
 
-func (m Model) BuildAccountView(availableHeight int) string {
-	leftWidth := 18
-	rightWidth := m.widthContent - leftWidth - 2 // 2 for gap
+// accountBodyHeight returns the inner content height of the account body
+// panels. The body is quantized to whole order cards so the menu panel's
+// bottom border lines up exactly with the last visible card; the two gap
+// rows around the body host the up/down scroll arrows.
+func (m Model) accountBodyHeight() int {
+	headerHeight := lipgloss.Height(m.BuildHeader())
+	footerHeight := lipgloss.Height(m.BuildFooter())
+	budget := m.heightContainer - headerHeight - footerHeight - 2
+	cards := budget / orderCardHeight
+	if cards < 1 {
+		cards = 1
+	}
+	return cards*orderCardHeight - 2
+}
 
-	// Build the left panel (menu items)
-	leftPanel := ""
+// accountDetailWidth returns the width of the unboxed detail area: the chrome
+// width minus the menu panel and the gap. The detail side has no outer panel
+// (its content draws its own boxes), so it reclaims the border + padding.
+func (m Model) accountDetailWidth() int {
+	contentW, menuW, _, _ := m.shopLayout()
+	if m.size < large {
+		return contentW
+	}
+	return contentW - (menuW + 4) - 1
+}
+
+// updateAccountViewport initializes or resizes the detail viewport for the account page.
+// The viewport spans the unboxed detail area to the right of the menu panel.
+func (m Model) updateAccountViewport() Model {
+	detailW := m.accountDetailWidth()
+	// +2: no panel on the detail side, so the viewport spans the same rows
+	// as the menu panel including its border rows — tops and bottoms align.
+	availableHeight := m.accountBodyHeight() + 2
+	if m.size < large {
+		// Stacked: the menu panel sits above the detail area
+		menuPanelHeight := len(models.AccountMenuItems) + 2
+		availableHeight -= menuPanelHeight
+		if availableHeight < 3 {
+			availableHeight = 3
+		}
+	}
+
+	if !m.account.viewportReady {
+		m.account.detailViewport = viewport.New(viewport.WithWidth(detailW), viewport.WithHeight(availableHeight))
+		m.account.detailViewport.KeyMap = modifiedKeyMap
+		m.account.viewportReady = true
+	} else {
+		m.account.detailViewport.SetWidth(detailW)
+		m.account.detailViewport.SetHeight(availableHeight)
+	}
+
+	return m
+}
+
+// getAccountDetailContent generates the content string for the current detail panel.
+func (m Model) getAccountDetailContent() string {
+	detailContentWidth := m.accountDetailWidth()
+
+	if m.account.cursor < 0 || m.account.cursor >= len(models.AccountMenuItems) {
+		return ""
+	}
+
+	selectedItem := models.AccountMenuItems[m.account.cursor]
+	switch selectedItem {
+	case "active orders":
+		return m.ActiveOrdersView(detailContentWidth)
+	case "order history":
+		return m.OrdersView(detailContentWidth)
+	case "addresses":
+		return m.AddressesView(detailContentWidth)
+	case "cards":
+		return m.CardsView(detailContentWidth)
+	case "faq":
+		questionStyle := m.theme.TextHighlight().Bold(true)
+		contentStyle := m.theme.TextBody().Width(detailContentWidth)
+		faqContent := ""
+		for i, faq := range m.FAQs {
+			faqContent += questionStyle.Render(wordWrap(faq.Question, detailContentWidth)) + "\n"
+			faqContent += contentStyle.Render(wordWrap(faq.Answer, detailContentWidth))
+			if i < len(m.FAQs)-1 {
+				faqContent += "\n\n"
+			}
+		}
+		detailView := faqContent
+		if !m.account.faqFocused {
+			hintStyle := m.theme.TextDim()
+			detailView += "\n\n" + hintStyle.Render("enter: scroll faq")
+		}
+		return detailView
+	case "about":
+		return m.AboutView(detailContentWidth)
+	}
+	return ""
+}
+
+// scrollToAccountDetailItem adjusts the viewport scroll to keep the selected item visible.
+// Follows the reference pattern: cursor moves immediately, viewport catches up.
+//
+// Each sub-page has a title header (e.g. "Order History" + margin + newlines) that
+// pushes the first item down. headerOffset accounts for those lines. itemHeight
+// must match the actual rendered card height including borders, padding, and the
+// inter-card gap ("\n" between cards in the view function).
+func (m Model) scrollToAccountDetailItem() Model {
+	var itemHeight, itemCount, selectedIndex, headerOffset int
+
+	switch {
+	case m.account.orderViewState == 1:
+		// Order list uses whole-card windowing instead of viewport scroll:
+		// shift the window just enough to keep the cursor's card visible.
+		page := m.orderListPageSize()
+		if m.account.orderCursor < m.account.orderWindowStart {
+			m.account.orderWindowStart = m.account.orderCursor
+		}
+		if m.account.orderCursor >= m.account.orderWindowStart+page {
+			m.account.orderWindowStart = m.account.orderCursor - page + 1
+		}
+		m.account.detailViewport.GotoTop()
+		return m
+	case m.account.addressListFocused:
+		// Titles were removed from the detail views, lists start at the top
+		headerOffset = 0
+		itemHeight = 5
+		itemCount = len(m.SavedAddresses)
+		selectedIndex = m.account.addressCursor
+	case m.account.cardListFocused:
+		headerOffset = 0
+		itemHeight = 4
+		itemCount = len(m.SavedCards)
+		selectedIndex = m.account.cardCursor
+	default:
+		return m
+	}
+
+	if itemCount == 0 {
+		return m
+	}
+
+	targetY := headerOffset + (selectedIndex * itemHeight)
+	vpH := m.account.detailViewport.Height()
+	offset := m.account.detailViewport.YOffset()
+
+	// 1-item buffer: scroll when the NEXT item would be off-screen,
+	// not when the current item hits the very edge
+	if targetY-itemHeight < offset {
+		m.account.detailViewport.SetYOffset(targetY - itemHeight)
+	}
+	if targetY+itemHeight+itemHeight > offset+vpH {
+		m.account.detailViewport.SetYOffset(targetY - vpH + itemHeight + itemHeight)
+	}
+
+	return m
+}
+
+func (m Model) BuildAccountView() string {
+	_, menuW, _, _ := m.shopLayout()
+
+	// Left panel: menu items. The highlight is blue while the user navigates
+	// the menu, and falls back to the gray pill when focus has moved into the
+	// detail area (browsing orders, managing addresses/cards, scrolling faq).
+	focusedInside := m.account.orderViewState > 0 || m.account.addressListFocused ||
+		m.account.cardListFocused || m.account.faqFocused
+	pillBg := m.theme.Highlight()
+	if focusedInside {
+		pillBg = cPill
+	}
+	var menu []string
 	for i, item := range models.AccountMenuItems {
 		if m.account.cursor == i {
-			style := m.theme.Base().Background(m.theme.Highlight()).Foreground(m.theme.Accent()).Padding(0, 1).Width(leftWidth - 2).Align(lipgloss.Left)
-			leftPanel += style.Render(item) + "\n"
+			menu = append(menu, lipgloss.NewStyle().Width(menuW).
+				Background(pillBg).Foreground(cWhite).Bold(true).
+				Render(" "+item))
 		} else {
-			style := m.theme.TextBody().Padding(0, 1).Width(leftWidth - 2).Align(lipgloss.Left)
-			leftPanel += style.Render(item) + "\n"
+			menu = append(menu, lipgloss.NewStyle().Width(menuW).
+				Render(" "+pBody.Render(item)))
 		}
 	}
+	menuContent := lipgloss.JoinVertical(lipgloss.Left, menu...)
 
-	leftContainer := m.theme.Base().
-		Width(leftWidth)
+	// Generate detail content and set it on the viewport
+	detailContent := m.getAccountDetailContent()
+	m.account.detailViewport.SetContent(detailContent)
 
-	// Build the detail view (right panel) based on cursor position
-	detailView := ""
-	if m.account.cursor >= 0 && m.account.cursor < len(models.AccountMenuItems) {
-		titleStyle := m.theme.TextAccent().Bold(true).MarginBottom(2)
+	// Viewport handles scrolling/clipping — no manual line-slicing needed
+	detailRendered := m.account.detailViewport.View()
 
-		// On small terminals, use full content width
-		detailContentWidth := rightWidth - 2
-		if m.size < large {
-			detailContentWidth = m.widthContent - 2
-		}
-
-		contentStyle := m.theme.TextBody().Width(detailContentWidth)
-
-		selectedItem := models.AccountMenuItems[m.account.cursor]
-		switch selectedItem {
-		case "order history":
-			if !m.OrdersLoaded {
-				detailView = titleStyle.Render("Order History") + "\n\n" + contentStyle.Render("Loading orders...")
-			} else if len(m.Orders) == 0 {
-				detailView = titleStyle.Render("Order History") + "\n\n" + contentStyle.Render("No orders yet.")
-			} else if m.account.orderViewState == 2 {
-				// State 2: full detail for the selected order
-				detailView = m.buildOrderDetailView(m.Orders[m.account.orderCursor], detailContentWidth)
-			} else {
-				// State 0 (preview) or State 1 (browsing with cursor)
-				boxWidth := detailContentWidth - 4
-				boxPadding := 0
-				if m.heightContainer >= 25 {
-					boxPadding = 1
-				}
-
-				lines := titleStyle.Render("Order History") + "\n\n"
-				for i, order := range m.Orders {
-					isSelected := m.account.orderViewState == 1 && i == m.account.orderCursor
-					lines += m.buildOrderCard(order, boxWidth, isSelected, boxPadding, detailContentWidth)
-					if i < len(m.Orders)-1 {
-						lines += "\n"
-					}
-				}
-
-				if m.account.orderViewState == 0 {
-					hintStyle := m.theme.TextDim()
-					lines += "\n" + hintStyle.Render("enter: browse orders")
-				}
-				detailView = lines
-			}
-
-		case "addresses":
-			lines := titleStyle.Render("Address") + "\n\n"
-			if len(m.SavedAddresses) == 0 {
-				lines += contentStyle.Render("No saved addresses")
-			} else {
-				for i, addr := range m.SavedAddresses {
-					isSelected := m.account.addressListFocused && i == m.account.addressCursor
-					label := addr.Name + "  " + addr.Street + ", " + addr.City
-					if len(label) > detailContentWidth-4 {
-						label = label[:detailContentWidth-4]
-					}
-					if m.account.addressDeleting != nil && *m.account.addressDeleting == i {
-						lines += m.theme.TextError().Bold(true).Render("  deletes? (y/n)") + "\n"
-					} else if isSelected {
-						lines += m.theme.TextAccent().Bold(true).Render("> "+label) + "\n"
-					} else {
-						lines += contentStyle.Render(" "+label) + "\n"
-					}
-				}
-			}
-			if m.account.addressListFocused {
-				lines += "\n" + m.theme.TextDim().Render("x: delete  esc: back")
-			} else {
-				lines += "\n" + m.theme.TextDim().Render("enter: manage")
-			}
-			detailView = lines
-
-		case "cards":
-			lines := titleStyle.Render("Cards") + "\n\n"
-			if len(m.SavedCards) == 0 {
-				lines += contentStyle.Render("No saved cards.")
-			} else {
-				for i, card := range m.SavedCards {
-					isSelected := m.account.cardListFocused && i == m.account.cardCursor
-					label := fmt.Sprintf("**** **** **** %s  %s  exp %02d/%02d",
-						card.Last4, card.Brand, card.ExpMonth, card.ExpYear%100)
-					if m.account.cardDeleting != nil && *m.account.cardDeleting == i {
-						lines += m.theme.TextError().Bold(true).Render("  delete? (y/n)") + "\n"
-					} else if isSelected {
-						lines += m.theme.TextAccent().Bold(true).Render("> "+label) + "\n"
-					} else {
-						lines += contentStyle.Render(" "+label) + "\n"
-					}
-				}
-			}
-			if m.account.cardListFocused {
-				lines += "\n" + m.theme.TextDim().Render("x: delete  esc: back")
-			} else {
-				lines += "\n" + m.theme.TextDim().Render("enter: manage")
-			}
-			detailView = lines
-
-		case "ssh keys":
-			lines := titleStyle.Render("SSH keys") + "\n\n"
-			if !m.SSHKeysLoaded {
-				lines += contentStyle.Render("Loading ssh keys...")
-			} else if len(m.SSHKeys) == 0 {
-				lines += contentStyle.Render("No saved ssh keys.")
-			} else {
-				for i, key := range m.SSHKeys {
-					isSelected := m.account.sshKeyListFocused && i == m.account.sshKeyCursor
-					label := key.Fingerprint
-					if key.Comment != "" {
-						label += "  " + key.Comment
-					}
-					if len(label) > detailContentWidth-4 {
-						label = label[:detailContentWidth-4]
-					}
-					if m.account.sshKeyDeleting != nil && *m.account.sshKeyDeleting == i {
-						lines += m.theme.TextError().Bold(true).Render("  delete? (y/n)") + "\n"
-					} else if isSelected {
-						lines += m.theme.TextAccent().Bold(true).Render("> "+label) + "\n"
-					} else {
-						lines += contentStyle.Render(" "+label) + "\n"
-					}
-				}
-			}
-			if m.account.sshKeyListFocused {
-				lines += "\n" + m.theme.TextDim().Render("x: delete  esc: back")
-			} else {
-				lines += "\n" + m.theme.TextDim().Render("enter: manage")
-			}
-			detailView = lines
-
-		case "faq":
-			questionStyle := m.theme.TextHighlight().Bold(true)
-
-			faqContent := ""
-			for i, faq := range m.FAQs {
-				faqContent += questionStyle.Render(wordWrap(faq.Question, detailContentWidth)) + "\n"
-				faqContent += contentStyle.Render(wordWrap(faq.Answer, detailContentWidth))
-				if i < len(m.FAQs)-1 {
-					faqContent += "\n\n"
-				}
-			}
-			detailView = titleStyle.Render("FAQ") + "\n\n" + faqContent
-			if !m.account.faqFocused {
-				hintStyle := m.theme.TextDim()
-				detailView += "\n\n" + hintStyle.Render("enter: scroll faq")
-			}
-		case "about":
-			accentStyle := m.theme.TextHighlight().Bold(true)
-			userStyle := m.theme.TextAccent().Bold(true)
-
-			aboutContent := contentStyle.Render(wordWrap(
-				"This project is heavily inspired by the wonderful team who made TerminalDotShop. I want to thank them for open-sourcing the code for that project. Cudos to those smart, funny, amazing looking devs:",
-				detailContentWidth,
-			)) + "\n\n"
-			aboutContent += userStyle.Render("@thdxr") + "\n"
-			aboutContent += userStyle.Render("@adamdotdev") + "\n"
-			aboutContent += userStyle.Render("@theprimeagen") + "\n"
-			aboutContent += userStyle.Render("@teej_dv") + "\n"
-			aboutContent += userStyle.Render("@iamdavidhill") + "\n\n"
-			aboutContent += contentStyle.Render("And me:") + "\n\n"
-			aboutContent += userStyle.Render("@marcusDenslow") + "\n\n"
-			aboutContent += contentStyle.Render(wordWrap("This project tries to copy the idea of terminalDotShop, but with one twist: write everything in GO. this is my humble attempt",
-				detailContentWidth)) + "\n"
-			aboutContent += accentStyle.Render("Terminal Products, Inc.")
-
-			detailView = titleStyle.Render("About") + "\n\n" + aboutContent
-
-		}
-	}
-
-	// Apply internal scrolling to just the detail view
-	// Scrolling is needed for: order detail/list and FAQ when focused
-	if m.account.orderViewState >= 1 || m.account.faqFocused {
-		detailLines := strings.Split(detailView, "\n")
-		totalLines := len(detailLines)
-
-		// In stacked mode, reduce available height by left panel
-		scrollHeight := availableHeight
-		if m.size < large {
-			leftPanelHeight := len(models.AccountMenuItems) + 1
-			scrollHeight = availableHeight - leftPanelHeight
-		}
-		if scrollHeight < 3 {
-			scrollHeight = 3
-		}
-
-		// Clamp scroll offset locally (don't mutate m since value receiver)
-		offset := m.account.scrollOffset
-		maxScroll := totalLines - scrollHeight
-		if maxScroll < 0 {
-			maxScroll = 0
-		}
-		if offset > maxScroll {
-			offset = maxScroll
-		}
-		if offset < 0 {
-			offset = 0
-		}
-
-		// Slice to visible window
-		if totalLines > scrollHeight {
-			end := offset + scrollHeight
-			if end > totalLines {
-				end = totalLines
-			}
-			detailLines = detailLines[offset:end]
-		}
-		detailView = strings.Join(detailLines, "\n")
-	}
-
-	detailContainer := lipgloss.NewStyle().
-		Width(rightWidth)
-
-	// Responsive layout: side-by-side on large, stacked on small/medium
+	// Responsive layout: menu panel beside the unboxed detail area on large,
+	// stacked on small/medium. The detail side draws its own item boxes.
+	var body string
 	if m.size < large {
-		return lipgloss.JoinVertical(
+		body = lipgloss.JoinVertical(
 			lipgloss.Left,
-			leftContainer.Render(leftPanel),
-			detailContainer.Width(m.widthContent).Render(detailView),
+			panel(menuW, 0, menuContent),
+			detailRendered,
+		)
+	} else {
+		bodyH := m.accountBodyHeight()
+		body = lipgloss.JoinHorizontal(
+			lipgloss.Top,
+			panel(menuW, bodyH, menuContent),
+			" ",
+			detailRendered,
 		)
 	}
 
-	return lipgloss.JoinHorizontal(
-		lipgloss.Top,
-		leftContainer.Render(leftPanel),
-		"  ",
-		detailContainer.Render(detailView),
-	)
+	// Blank rows separate the body from the header and footer boxes. When the
+	// windowed order list has hidden items, the arrows occupy those gap rows,
+	// centered over the card column, so the cards themselves always span
+	// exactly the menu panel's rows — top and bottom borders aligned.
+	topGap := ""
+	if above := m.orderHiddenAbove(); above > 0 && m.size >= large {
+		topGap = strings.Repeat(" ", menuW+5) +
+			orderScrollIndicator("↑", above, m.accountDetailWidth())
+	}
+	bottomGap := ""
+	if below := m.orderHiddenBelow(); below > 0 && m.size >= large {
+		bottomGap = strings.Repeat(" ", menuW+5) +
+			orderScrollIndicator("↓", below, m.accountDetailWidth())
+	}
+	return topGap + "\n" + body + "\n" + bottomGap
 }
 
-// buildOrderCard renders a single order as a bordered box for the order list.
-// Shows order number, date, status, total, and the first 2 items as a preview.
-func (m Model) buildOrderCard(order models.Order, boxWidth int, isSelected bool, boxPadding int, containerWidth int) string {
-	// Order header line: "Order #123" left, "Jan 02 2026  PAID" right
-	nameStyle := m.theme.TextAccent().Bold(true)
+func (m Model) AboutView(width int) string {
+	contentStyle := m.theme.TextBody().Width(width)
+	// USE this if wanting to add a corp name later
+	// accentStyle := m.theme.TextHighlight().Bold(true)
+	userStyle := m.theme.TextAccent().Bold(true)
 
-	dimStyle := m.theme.TextDim()
+	aboutContent := contentStyle.Render(wordWrap(
+		"This project is heavily inspired by the wonderful team who made TerminalDotShop. I want to thank them for open-sourcing the code for that project. Cudos to those smart, funny, amazing looking devs:",
+		width,
+	)) + "\n\n"
+	aboutContent += userStyle.Render("@thdxr") + "\n"
+	aboutContent += userStyle.Render("@adamdotdev") + "\n"
+	aboutContent += userStyle.Render("@theprimeagen") + "\n"
+	aboutContent += userStyle.Render("@teej_dv") + "\n"
+	aboutContent += userStyle.Render("@iamdavidhill") + "\n\n"
+	aboutContent += contentStyle.Render("And me:") + "\n\n"
+	aboutContent += userStyle.Render("@marcusDenslow") + "\n\n"
+	aboutContent += contentStyle.Render(wordWrap(
+		"This project tries to copy the idea of terminalDotShop, but with one twist: write everything in GO. this is my humble attempt",
+		width,
+	)) + "\n"
 
-	statusStyle := m.theme.TextHighlight().Bold(true)
-
-	orderLabel := nameStyle.Render(fmt.Sprintf("Order #%d", order.ID))
-	total := nameStyle.Render(fmt.Sprintf("$%.2f", float64(order.Total)/100.0))
-	date := dimStyle.Render(order.CreatedAt.Format("Jan 02 2006"))
-	status := statusStyle.Render(strings.ToUpper(string(order.Status)))
-
-	rightSide := date + "  " + status + "  " + total
-	rightWidth := lipgloss.Width(rightSide)
-	leftWidth := lipgloss.Width(orderLabel)
-	spacing := boxWidth - leftWidth - rightWidth - 4 // 4 for padding
-	if spacing < 1 {
-		spacing = 1
-	}
-
-	line1 := orderLabel + lipgloss.NewStyle().Width(spacing).Render("") + rightSide
-
-	// Item preview lines (show first 2 items)
-	var lines []string
-	lines = append(lines, line1)
-
-	previewCount := 2
-	if len(order.Items) < previewCount {
-		previewCount = len(order.Items)
-	}
-	for i := 0; i < previewCount; i++ {
-		item := order.Items[i]
-		itemLine := dimStyle.Render(fmt.Sprintf("%dx %s - $%.2f", item.Quantity, item.Name, float64(item.Price)/100.0))
-		lines = append(lines, itemLine)
-	}
-	if len(order.Items) > 2 {
-		extra := len(order.Items) - 2
-		moreText := "item"
-		if extra > 1 {
-			moreText = "items"
-		}
-		lines = append(lines, dimStyle.Render(fmt.Sprintf("+ %d more %s", extra, moreText)))
-	}
-
-	boxContent := strings.Join(lines, "\n")
-
-	// Create bordered box — highlight if selected
-	var itemBox lipgloss.Style
-	if isSelected {
-		itemBox = lipgloss.NewStyle().
-			Border(lipgloss.NormalBorder(), true).
-			BorderForeground(m.theme.Accent()).
-			Padding(boxPadding, 2).
-			Width(boxWidth)
-	} else {
-		itemBox = lipgloss.NewStyle().
-			Border(lipgloss.NormalBorder()).
-			BorderForeground(m.theme.Border()).
-			Padding(boxPadding, 2).
-			Width(boxWidth)
-	}
-
-	centered := lipgloss.NewStyle().
-		Width(containerWidth).
-		Align(lipgloss.Center)
-
-	return centered.Render(itemBox.Render(boxContent))
-}
-
-// buildOrderDetailView renders the full detail view for a single order.
-func (m Model) buildOrderDetailView(order models.Order, width int) string {
-	titleStyle := m.theme.TextAccent().Bold(true).MarginBottom(1)
-
-	labelStyle := m.theme.TextHighlight().Bold(true)
-
-	valueStyle := m.theme.TextBody()
-
-	dimStyle := m.theme.TextDim()
-
-	var b strings.Builder
-
-	// Header
-	b.WriteString(titleStyle.Render(fmt.Sprintf("Order #%d", order.ID)))
-	b.WriteString("\n\n")
-
-	// Status and date
-	b.WriteString(labelStyle.Render("Status:  "))
-	b.WriteString(valueStyle.Render(strings.ToUpper(string(order.Status))))
-	b.WriteString("\n")
-	b.WriteString(labelStyle.Render("Date:    "))
-	b.WriteString(valueStyle.Render(order.CreatedAt.Format("Jan 02 2006 3:04 PM")))
-	b.WriteString("\n\n")
-
-	// Items
-	b.WriteString(labelStyle.Render("Items"))
-	b.WriteString("\n")
-	b.WriteString(dimStyle.Render(strings.Repeat("-", 40)))
-	b.WriteString("\n")
-	for _, item := range order.Items {
-		price := fmt.Sprintf("$%.2f", float64(item.Price)/100.0)
-		line := fmt.Sprintf("  %dx %-20s %s", item.Quantity, item.Name, price)
-		b.WriteString(valueStyle.Render(line))
-		b.WriteString("\n")
-	}
-	b.WriteString(dimStyle.Render(strings.Repeat("-", 40)))
-	b.WriteString("\n")
-
-	// Totals
-	subtotal := fmt.Sprintf("$%.2f", float64(order.Subtotal)/100.0)
-	shipping := fmt.Sprintf("$%.2f", float64(order.ShippingCost)/100.0)
-	total := fmt.Sprintf("$%.2f", float64(order.Total)/100.0)
-	b.WriteString(valueStyle.Render(fmt.Sprintf("  %-22s %s", "Subtotal", subtotal)))
-	b.WriteString("\n")
-	b.WriteString(valueStyle.Render(fmt.Sprintf("  %-22s %s", "Shipping", shipping)))
-	b.WriteString("\n")
-	b.WriteString(labelStyle.Render(fmt.Sprintf("  %-22s %s", "Total", total)))
-	b.WriteString("\n\n")
-
-	// Shipping address
-	b.WriteString(labelStyle.Render("Ship To"))
-	b.WriteString("\n")
-	b.WriteString(valueStyle.Render("  " + order.ShippingName))
-	b.WriteString("\n")
-	b.WriteString(valueStyle.Render("  " + order.ShippingStreet))
-	b.WriteString("\n")
-	if order.ShippingStreet2 != "" {
-		b.WriteString(valueStyle.Render("  " + order.ShippingStreet2))
-		b.WriteString("\n")
-	}
-	cityLine := order.ShippingCity
-	if order.ShippingState != "" {
-		cityLine += ", " + order.ShippingState
-	}
-	cityLine += " " + order.ShippingZip
-	b.WriteString(valueStyle.Render("  " + cityLine))
-	b.WriteString("\n")
-	b.WriteString(valueStyle.Render("  " + order.ShippingCountry))
-	b.WriteString("\n\n")
-
-	// Footer hint
-	b.WriteString(dimStyle.Render("esc: back to orders"))
-
-	return b.String()
-}
-
-// computeFaqScrollMax calculates the maximum scroll offset for the FAQ content.
-// This renders the FAQ the same way BuildAccountView does, counts the lines,
-// and returns the max scroll value. Returns 0 if no scrolling is needed.
-func (m Model) computeFaqScrollMax() int {
-	leftWidth := 18
-	rightWidth := m.widthContent - leftWidth - 2
-	detailContentWidth := rightWidth - 2
-	if m.size < large {
-		detailContentWidth = m.widthContent - 2
-	}
-
-	questionStyle := m.theme.TextHighlight().Bold(true)
-	contentStyle := m.theme.TextBody().Width(detailContentWidth)
-
-	faqContent := ""
-	for i, faq := range m.FAQs {
-		faqContent += questionStyle.Render(wordWrap(faq.Question, detailContentWidth)) + "\n"
-		faqContent += contentStyle.Render(wordWrap(faq.Answer, detailContentWidth))
-		if i < len(m.FAQs)-1 {
-			faqContent += "\n\n"
-		}
-	}
-
-	titleStyle := m.theme.TextAccent().Bold(true).MarginBottom(2)
-	detailView := titleStyle.Render("FAQ") + "\n\n" + faqContent
-
-	totalLines := len(strings.Split(detailView, "\n"))
-
-	scrollHeight := m.heightContainer - 7
-	if m.size < large {
-		scrollHeight -= len(models.AccountMenuItems) + 1
-	}
-	if scrollHeight < 3 {
-		scrollHeight = 3
-	}
-
-	maxScroll := totalLines - scrollHeight
-	if maxScroll < 0 {
-		maxScroll = 0
-	}
-	return maxScroll
+	return aboutContent
 }
 
 func (m Model) AccountUpdate(msg tea.Msg) (Model, tea.Cmd) {
 	keyMsg, ok := msg.(tea.KeyMsg)
 	if !ok {
-		return m, nil
+		// Pass non-key messages to viewport (e.g. window resize)
+		var cmd tea.Cmd
+		m.account.detailViewport, cmd = m.account.detailViewport.Update(msg)
+		return m, cmd
 	}
 
 	selectedItem := ""
@@ -464,93 +272,71 @@ func (m Model) AccountUpdate(msg tea.Msg) (Model, tea.Cmd) {
 
 	switch keyMsg.String() {
 	case "up", "k":
+		// In order detail or FAQ, scroll the viewport directly
+		if m.account.orderViewState == 2 || m.account.faqFocused {
+			m.account.detailViewport.SetContent(m.getAccountDetailContent())
+			m.account.detailViewport.ScrollUp(3)
+			return m, nil
+		}
 		if m.account.addressListFocused && m.account.addressDeleting == nil {
 			if m.account.addressCursor > 0 {
 				m.account.addressCursor--
+				m.account.detailViewport.SetContent(m.getAccountDetailContent())
+				m = m.scrollToAccountDetailItem()
 			}
 		} else if m.account.cardListFocused && m.account.cardDeleting == nil {
 			if m.account.cardCursor > 0 {
 				m.account.cardCursor--
-			}
-		} else if m.account.sshKeyListFocused && m.account.sshKeyDeleting == nil {
-			if m.account.sshKeyCursor > 0 {
-				m.account.sshKeyCursor--
-			}
-		} else if m.account.faqFocused {
-			m.account.scrollOffset -= 3
-			if m.account.scrollOffset < 0 {
-				m.account.scrollOffset = 0
+				m.account.detailViewport.SetContent(m.getAccountDetailContent())
+				m = m.scrollToAccountDetailItem()
 			}
 		} else if m.account.orderViewState == 1 && m.account.orderCursor > 0 {
 			m.account.orderCursor--
-			cardHeight := 5
-			if m.heightContainer >= 25 {
-				cardHeight = 7
-			}
-			targetTop := 3 + m.account.orderCursor*cardHeight
-			if targetTop < m.account.scrollOffset {
-				m.account.scrollOffset = targetTop
-			}
+			m.account.detailViewport.SetContent(m.getAccountDetailContent())
+			m = m.scrollToAccountDetailItem()
 		} else if m.account.orderViewState == 0 && m.account.cursor > 0 {
 			m.account.cursor--
-			m.account.scrollOffset = 0
+			m.account.detailViewport.GotoTop()
 		}
 
 	case "down", "j":
+		if m.account.orderViewState == 2 || m.account.faqFocused {
+			m.account.detailViewport.SetContent(m.getAccountDetailContent())
+			m.account.detailViewport.ScrollDown(3)
+			return m, nil
+		}
 		if m.account.addressListFocused && m.account.addressDeleting == nil {
 			if m.account.addressCursor < len(m.SavedAddresses)-1 {
 				m.account.addressCursor++
+				m.account.detailViewport.SetContent(m.getAccountDetailContent())
+				m = m.scrollToAccountDetailItem()
 			}
 		} else if m.account.cardListFocused && m.account.cardDeleting == nil {
 			if m.account.cardCursor < len(m.SavedCards)-1 {
 				m.account.cardCursor++
+				m.account.detailViewport.SetContent(m.getAccountDetailContent())
+				m = m.scrollToAccountDetailItem()
 			}
-		} else if m.account.sshKeyListFocused && m.account.sshKeyDeleting == nil {
-			if m.account.sshKeyCursor < len(m.SSHKeys)-1 {
-				m.account.sshKeyCursor++
-			}
-		} else if m.account.faqFocused {
-			m.account.scrollOffset += 3
-			maxScroll := m.computeFaqScrollMax()
-			if m.account.scrollOffset > maxScroll {
-				m.account.scrollOffset = maxScroll
-			}
-		} else if m.account.orderViewState == 1 && m.account.orderCursor < len(m.Orders)-1 {
+		} else if m.account.orderViewState == 1 && m.account.orderCursor < len(m.currentOrderList())-1 {
 			m.account.orderCursor++
-			cardHeight := 5
-			if m.heightContainer >= 25 {
-				cardHeight = 7
-			}
-			viewportHeight := m.heightContainer - 7
-			if m.size < large {
-				viewportHeight -= len(models.AccountMenuItems) + 1
-			}
-			if viewportHeight < 5 {
-				viewportHeight = 5
-			}
-			targetBottom := 3 + (m.account.orderCursor+1)*cardHeight
-			if targetBottom > m.account.scrollOffset+viewportHeight {
-				m.account.scrollOffset = targetBottom - viewportHeight
-			}
-		} else if m.account.orderViewState == 0 && !m.account.addressListFocused && !m.account.cardListFocused && !m.account.sshKeyListFocused && m.account.cursor < len(models.AccountMenuItems)-1 {
+			m.account.detailViewport.SetContent(m.getAccountDetailContent())
+			m = m.scrollToAccountDetailItem()
+		} else if m.account.orderViewState == 0 && !m.account.addressListFocused && !m.account.cardListFocused && m.account.cursor < len(models.AccountMenuItems)-1 {
 			m.account.cursor++
-			m.account.scrollOffset = 0
+			m.account.detailViewport.GotoTop()
 		}
 
-	case "pgup", "ctrl+u":
-		if m.account.faqFocused || m.account.orderViewState >= 2 {
-			m.account.scrollOffset -= 3
-			if m.account.scrollOffset < 0 {
-				m.account.scrollOffset = 0
-			}
-		}
+	case "pgup", "ctrl+u", "pgdown", "ctrl+d":
+		// Ensure viewport has content before delegating scroll
+		m.account.detailViewport.SetContent(m.getAccountDetailContent())
+		var cmd tea.Cmd
+		m.account.detailViewport, cmd = m.account.detailViewport.Update(msg)
+		return m, cmd
 
-	case "pgdown", "ctrl+d":
-		if m.account.faqFocused || m.account.orderViewState >= 2 {
-			m.account.scrollOffset += 3
-			maxScroll := m.computeFaqScrollMax()
-			if m.account.faqFocused && maxScroll >= 0 && m.account.scrollOffset > maxScroll {
-				m.account.scrollOffset = maxScroll
+	case "r":
+		if m.account.orderViewState == 2 {
+			if order, ok := m.selectedRefundableOrder(); ok {
+				return m.OpenRefundComposer(order.ID)
 			}
 		}
 
@@ -559,8 +345,6 @@ func (m Model) AccountUpdate(msg tea.Msg) (Model, tea.Cmd) {
 			m.account.addressDeleting = &m.account.addressCursor
 		} else if m.account.cardListFocused && m.account.cardDeleting == nil && m.account.cardCursor < len(m.SavedCards) {
 			m.account.cardDeleting = &m.account.cardCursor
-		} else if m.account.sshKeyListFocused && m.account.sshKeyDeleting == nil && m.account.sshKeyCursor < len(m.SSHKeys) {
-			m.account.sshKeyDeleting = &m.account.sshKeyCursor
 		}
 
 	case "y":
@@ -582,79 +366,121 @@ func (m Model) AccountUpdate(msg tea.Msg) (Model, tea.Cmd) {
 				m.account.cardCursor--
 			}
 			return m, m.deleteCardCmd(card.ID)
-		} else if m.account.sshKeyDeleting != nil {
-			cursor := *m.account.sshKeyDeleting
-			key := m.SSHKeys[cursor]
-			m.account.sshKeyDeleting = nil
-			m.SSHKeys = append(m.SSHKeys[:cursor], m.SSHKeys[cursor+1:]...)
-			if m.account.sshKeyCursor >= len(m.SSHKeys) && m.account.sshKeyCursor > 0 {
-				m.account.sshKeyCursor--
-			}
-			return m, m.deleteSSHKeyCmd(key.ID)
 		}
 
 	case "n":
 		m.account.addressDeleting = nil
 		m.account.cardDeleting = nil
-		m.account.sshKeyDeleting = nil
 
 	case "p", "enter":
 		switch selectedItem {
-		case "order history":
-			if len(m.Orders) > 0 {
-				if m.account.orderViewState == 0 {
+		case "order history", "active orders":
+			if len(m.currentOrderList()) > 0 {
+				switch m.account.orderViewState {
+				case 0:
 					m.account.orderViewState = 1
 					m.account.orderCursor = 0
-					m.account.scrollOffset = 0
-				} else if m.account.orderViewState == 1 {
+					m.account.orderWindowStart = 0
+					m.account.detailViewport.GotoTop()
+					m.footer = []footerCommand{
+						{key: "j/k", value: "orders"},
+						{key: "enter", value: "details"},
+						{key: "esc", value: "back"},
+						{key: "q", value: "quit"},
+					}
+				case 1:
+					m.account.orderYOffset = m.account.detailViewport.YOffset()
 					m.account.orderViewState = 2
-					m.account.scrollOffset = 0
+					m.account.detailViewport.GotoTop()
+					footer := []footerCommand{
+						{key: "esc", value: "back"},
+						{key: "s", value: "shop"},
+						{key: "q", value: "quit"},
+					}
+					if _, ok := m.selectedRefundableOrder(); ok {
+						footer = append([]footerCommand{{key: "r", value: "refund"}}, footer...)
+					}
+					m.footer = footer
 				}
 			}
-		case "ssh keys":
-			if !m.account.sshKeyListFocused {
-				m.account.sshKeyListFocused = true
-				m.account.sshKeyCursor = 0
-			}
 		case "addresses":
 			if !m.account.addressListFocused {
 				m.account.addressListFocused = true
 				m.account.addressCursor = 0
+				m.footer = []footerCommand{
+					{key: "j/k", value: "addresses"},
+					{key: "x", value: "delete"},
+					{key: "esc", value: "back"},
+				}
 			}
 		case "cards":
 			if !m.account.cardListFocused {
 				m.account.cardListFocused = true
 				m.account.cardCursor = 0
+				m.footer = []footerCommand{
+					{key: "j/k", value: "cards"},
+					{key: "x", value: "delete"},
+					{key: "esc", value: "back"},
+				}
 			}
 		case "faq":
 			if !m.account.faqFocused {
 				m.account.faqFocused = true
-				m.account.scrollOffset = 0
+				m.account.detailViewport.GotoTop()
+				m.footer = []footerCommand{
+					{key: "j/k", value: "scroll"},
+					{key: "esc", value: "back"},
+					{key: "s", value: "shop"},
+					{key: "c", value: "cart"},
+					{key: "q", value: "quit"},
+				}
 			}
 		}
 
 	case "esc":
+		accountDefaultFooter := []footerCommand{
+			{key: "j/k", value: "navigate"},
+			{key: "enter", value: "select"},
+			{key: "s", value: "shop"},
+			{key: "c", value: "cart"},
+			{key: "?", value: "help"},
+			{key: "q", value: "quit"},
+		}
 		if m.account.addressDeleting != nil {
 			m.account.addressDeleting = nil
 		} else if m.account.addressListFocused {
 			m.account.addressListFocused = false
 			m.account.addressCursor = 0
+			m.footer = accountDefaultFooter
 		} else if m.account.cardDeleting != nil {
 			m.account.cardDeleting = nil
 		} else if m.account.cardListFocused {
 			m.account.cardListFocused = false
 			m.account.cardCursor = 0
-		} else if m.account.sshKeyDeleting != nil {
-			m.account.sshKeyDeleting = nil
-		} else if m.account.sshKeyListFocused {
-			m.account.sshKeyListFocused = false
-			m.account.sshKeyCursor = 0
+			m.footer = accountDefaultFooter
 		} else if m.account.faqFocused {
 			m.account.faqFocused = false
-			m.account.scrollOffset = 0
+			m.account.detailViewport.GotoTop()
+			m.footer = accountDefaultFooter
 		} else if m.account.orderViewState > 0 {
 			m.account.orderViewState--
-			m.account.scrollOffset = 0
+			if m.account.orderViewState == 1 {
+				// Set content first so SetYOffset can clamp against correct line count
+				m.account.detailViewport.SetContent(m.getAccountDetailContent())
+				if m.account.orderYOffset > 0 {
+					m.account.detailViewport.SetYOffset(m.account.orderYOffset)
+					m.account.orderYOffset = 0
+				}
+				m.footer = []footerCommand{
+					{key: "j/k", value: "orders"},
+					{key: "enter", value: "details"},
+					{key: "esc", value: "back"},
+					{key: "q", value: "quit"},
+				}
+			} else {
+				m.account.detailViewport.GotoTop()
+				m.footer = accountDefaultFooter
+			}
 		}
 	}
 	return m, nil

pkg/tui/account_addresses.go

@@ -0,0 +1,29 @@
+package tui
+
+func (m Model) AddressesView(width int) string {
+	contentStyle := m.theme.TextBody().Width(width)
+
+	lines := ""
+	if len(m.SavedAddresses) == 0 {
+		lines += contentStyle.Render("No saved addresses")
+	} else {
+		for i, addr := range m.SavedAddresses {
+			isSelected := m.account.addressListFocused && i == m.account.addressCursor
+			label := addr.Name + "  " + addr.Street + ", " + addr.City
+			if len(label) > width-4 {
+				label = label[:width-4]
+			}
+			if m.account.addressDeleting != nil && *m.account.addressDeleting == i {
+				lines += m.theme.TextError().Bold(true).Render("  deletes? (y/n)") + "\n"
+			} else {
+				lines += m.formatListItemCustom(label, isSelected, width, true) + "\n"
+			}
+		}
+	}
+	if m.account.addressListFocused {
+		lines += "\n" + m.theme.TextDim().Render("x: delete  esc: back")
+	} else {
+		lines += "\n" + m.theme.TextDim().Render("enter: manage")
+	}
+	return lines
+}

pkg/tui/account_cards.go

@@ -0,0 +1,31 @@
+package tui
+
+import (
+	"fmt"
+)
+
+func (m Model) CardsView(width int) string {
+	contentStyle := m.theme.TextBody().Width(width)
+
+	lines := ""
+	if m.SavedCardsIsEmpty() {
+		lines += contentStyle.Render("No saved cards")
+	} else {
+		for i, card := range m.SavedCards {
+			isSelected := m.account.cardListFocused && i == m.account.cardCursor
+			label := fmt.Sprintf("**** **** **** %s  %s  exp %02d/%02d", card.Last4, card.Brand, card.ExpMonth, card.ExpYear%100)
+			if m.account.cardDeleting != nil && *m.account.cardDeleting == i {
+				lines += m.theme.TextError().Bold(true).Render(" delete? (y/s)") + "\n"
+			} else {
+				lines += m.formatListItemCustom(label, isSelected, width, true) + "\n"
+			}
+		}
+	}
+	if m.account.cardListFocused {
+		lines += "\n" + m.theme.TextDim().Render("x: delete  esc: back")
+	} else {
+		lines += "\n" + m.theme.TextDim().Render("enter: manage")
+	}
+
+	return lines
+}

pkg/tui/account_orders.go

@@ -0,0 +1,340 @@
+package tui
+
+import (
+	"fmt"
+	"strings"
+
+	"terminalShop/pkg/models"
+
+	"charm.land/lipgloss/v2"
+)
+
+func (m Model) OrdersView(width int) string {
+	return m.orderListView(m.HistoryOrders(), width)
+}
+
+func (m Model) ActiveOrdersView(width int) string {
+	return m.orderListView(m.ActiveOrders(), width)
+}
+
+func (m Model) ActiveOrders() []models.Order {
+	out := make([]models.Order, 0, len(m.Orders))
+	for _, o := range m.Orders {
+		if o.IsActive() {
+			out = append(out, o)
+		}
+	}
+	return out
+}
+
+func (m Model) HistoryOrders() []models.Order {
+	out := make([]models.Order, 0, len(m.Orders))
+	for _, o := range m.Orders {
+		if !o.IsActive() {
+			out = append(out, o)
+		}
+	}
+	return out
+}
+
+// selectedRefundableOrder returns the order under the cursor in the active
+// order-detail view, paired with ok=true, when the user is allowed to file a
+// refund request for it. Returns (zero, false) otherwise.
+func (m Model) selectedRefundableOrder() (models.Order, bool) {
+	orders := m.currentOrderList()
+	if m.account.orderCursor < 0 || m.account.orderCursor >= len(orders) {
+		return models.Order{}, false
+	}
+	order := orders[m.account.orderCursor]
+	if !order.CanRequestRefund() {
+		return models.Order{}, false
+	}
+	return order, true
+}
+
+func (m Model) currentOrderList() []models.Order {
+	if m.account.cursor < 0 || m.account.cursor >= len(models.AccountMenuItems) {
+		return nil
+	}
+	switch models.AccountMenuItems[m.account.cursor] {
+	case "active orders":
+		return m.ActiveOrders()
+	case "order history":
+		return m.HistoryOrders()
+	}
+	return nil
+}
+
+// orderCardHeight is the rendered height of one order card:
+// border (2) + content lines (2), no vertical padding.
+const orderCardHeight = 4
+
+// orderListPageSize returns how many whole order cards fit in the detail
+// area. Both scroll arrows render outside the list, in the gap rows above
+// and below the body, so the cards use the full viewport height.
+func (m Model) orderListPageSize() int {
+	n := m.account.detailViewport.Height() / orderCardHeight
+	if n < 1 {
+		n = 1
+	}
+	return n
+}
+
+// orderHiddenAbove returns how many order cards are scrolled off above the
+// windowed list, or 0 when the windowed order list isn't showing.
+func (m Model) orderHiddenAbove() int {
+	if m.account.orderViewState != 1 || !m.OrdersLoaded {
+		return 0
+	}
+	orders := m.currentOrderList()
+	if len(orders) == 0 {
+		return 0
+	}
+	page := m.orderListPageSize()
+	start := m.account.orderWindowStart
+	if start > len(orders)-page {
+		start = len(orders) - page
+	}
+	if start < 0 {
+		start = 0
+	}
+	return start
+}
+
+// orderHiddenBelow returns how many order cards are scrolled off below the
+// windowed list, or 0 when the windowed order list isn't showing.
+func (m Model) orderHiddenBelow() int {
+	if m.account.orderViewState == 2 || !m.OrdersLoaded {
+		return 0
+	}
+	orders := m.currentOrderList()
+	if len(orders) == 0 {
+		return 0
+	}
+	below := len(orders) - (m.orderHiddenAbove() + m.orderListPageSize())
+	if below < 0 {
+		below = 0
+	}
+	return below
+}
+
+// orderScrollIndicator renders the dim "more items" arrow row, centered
+// across the card width.
+func orderScrollIndicator(arrow string, count, width int) string {
+	return pDim.Width(width).Align(lipgloss.Center).
+		Render(fmt.Sprintf("%s %d more", arrow, count))
+}
+
+func (m Model) orderListView(orders []models.Order, width int) string {
+	contentStyle := m.theme.TextBody().Width(width)
+
+	if !m.OrdersLoaded {
+		return contentStyle.Render("Loading orders...")
+	}
+	if len(orders) == 0 {
+		return contentStyle.Render("No orders yet")
+	}
+	if m.account.orderViewState == 2 {
+		return m.buildOrderDetailView(orders[m.account.orderCursor], width)
+	}
+
+	// Whole-card windowing: render only fully-visible cards, never clipping a
+	// card mid-border. Both scroll arrows render in BuildAccountView's gap
+	// rows, so the cards span exactly the menu panel's rows.
+	page := m.orderListPageSize()
+	start := m.orderHiddenAbove()
+	end := start + page
+	if end > len(orders) {
+		end = len(orders)
+	}
+
+	var rows []string
+	for i := start; i < end; i++ {
+		isSelected := m.account.orderViewState == 1 && i == m.account.orderCursor
+		rows = append(rows, m.buildOrderCard(orders[i], width, isSelected))
+	}
+	return lipgloss.JoinVertical(lipgloss.Left, rows...)
+}
+
+// buildOrderCard renders a single order as a bordered box with fixed height.
+// Shows order number + total on line 1, date + status on line 2.
+// Item details are shown in the detail view (viewState 2).
+func (m Model) buildOrderCard(order models.Order, boxWidth int, isSelected bool) string {
+	nameStyle := m.theme.TextDim()
+	if isSelected {
+		nameStyle = m.theme.TextAccent().Bold(true)
+	}
+
+	// When selected, secondary text uses accent color so the whole card "lights up"
+	dimStyle := m.theme.TextDim()
+	if isSelected {
+		dimStyle = m.theme.TextAccent()
+	}
+
+	// Line 1: "Order #N" left, "$X.XX" right
+	orderLabel := nameStyle.Render(fmt.Sprintf("Order #%d", order.ID))
+	total := nameStyle.Render(fmt.Sprintf("$%.2f", float64(order.Total)/100.0))
+
+	innerWidth := boxWidth - 4 // account for border + padding
+	leftWidth := lipgloss.Width(orderLabel)
+	rightWidth := lipgloss.Width(total)
+	spacing := innerWidth - leftWidth - rightWidth
+	if spacing < 1 {
+		spacing = 1
+	}
+	line1 := orderLabel + lipgloss.NewStyle().Width(spacing).Render("") + total
+
+	// Line 2: date + derived status
+	date := dimStyle.Render(order.CreatedAt.Format("Jan 02 2006"))
+	status := m.displayStyle(order.DisplayKind()).Bold(true).Render(order.DisplayState())
+	line2 := date + "  " + status
+
+	boxContent := line1 + "\n" + line2
+
+	return m.CreateBoxCustom(boxContent, isSelected, boxWidth)
+}
+
+// buildOrderDetailView renders the full detail view for a single order
+func (m Model) buildOrderDetailView(order models.Order, _ int) string {
+	titleStyle := m.theme.TextAccent().Bold(true).MarginBottom(1)
+
+	labelStyle := m.theme.TextHighlight().Bold(true)
+
+	valueStyle := m.theme.TextBody()
+
+	dimStyle := m.theme.TextDim()
+
+	var b strings.Builder
+
+	// Header
+	b.WriteString(titleStyle.Render(fmt.Sprintf("Order #%d", order.ID)))
+	b.WriteString("\n\n")
+
+	// Status and date
+	b.WriteString(labelStyle.Render("Status:  "))
+	b.WriteString(m.displayStyle(order.DisplayKind()).Render(order.DisplayState()))
+	b.WriteString("\n")
+	if order.TrackingStatusDetails != "" {
+		b.WriteString(dimStyle.Render("         " + order.TrackingStatusDetails))
+		b.WriteString("\n")
+	}
+	b.WriteString(labelStyle.Render("Date:    "))
+	b.WriteString(valueStyle.Render(order.CreatedAt.Format("Jan 02 2006 3:04 PM")))
+	b.WriteString("\n\n")
+
+	// Items
+	b.WriteString(labelStyle.Render("Items"))
+	b.WriteString("\n")
+	b.WriteString(dimStyle.Render(strings.Repeat("-", 40)))
+	b.WriteString("\n")
+	for _, item := range order.Items {
+		price := fmt.Sprintf("$%.2f", float64(item.Price)/100.0)
+		line := fmt.Sprintf("  %dx %-20s %s", item.Quantity, item.Name, price)
+		b.WriteString(valueStyle.Render(line))
+		b.WriteString("\n")
+	}
+	b.WriteString(dimStyle.Render(strings.Repeat("-", 40)))
+	b.WriteString("\n")
+
+	// Totals
+	subtotal := fmt.Sprintf("$%.2f", float64(order.Subtotal)/100.0)
+	shipping := fmt.Sprintf("$%.2f", float64(order.ShippingCost)/100.0)
+	total := fmt.Sprintf("$%.2f", float64(order.Total)/100.0)
+	b.WriteString(valueStyle.Render(fmt.Sprintf("  %-22s %s", "Subtotal", subtotal)))
+	b.WriteString("\n")
+	b.WriteString(valueStyle.Render(fmt.Sprintf("  %-22s %s", "Shipping", shipping)))
+	b.WriteString("\n")
+	b.WriteString(labelStyle.Render(fmt.Sprintf("  %-22s %s", "Total", total)))
+	b.WriteString("\n\n")
+
+	// Shipping (only when at least one shipment exists)
+	if order.Carrier != "" {
+		b.WriteString(labelStyle.Render("Shipping"))
+		b.WriteString("\n")
+		b.WriteString(valueStyle.Render(fmt.Sprintf("  %-10s %s", "Carrier", order.Carrier)))
+		b.WriteString("\n")
+		b.WriteString(valueStyle.Render(fmt.Sprintf("  %-10s %s", "Tracking", order.TrackingNumber)))
+		b.WriteString("\n")
+		if order.TrackingStatus != "" {
+			b.WriteString(valueStyle.Render(fmt.Sprintf("  %-10s %s", "Status", string(order.TrackingStatus))))
+			b.WriteString("\n")
+		}
+		if order.ShippedAt != nil {
+			b.WriteString(valueStyle.Render(fmt.Sprintf("  %-10s %s",
+				"Shipped", order.ShippedAt.Format("Jan 02 2006"))))
+			b.WriteString("\n")
+		}
+		if order.TrackingURL != "" {
+			b.WriteString(dimStyle.Render(fmt.Sprintf("  https://api.sshops.uk/t/%d", order.ID)))
+			b.WriteString("\n")
+		}
+	}
+
+	visible := make([]models.OrderEvent, 0, len(order.Events))
+	for _, event := range order.Events {
+		if _, ok := event.DisplayLabel(); ok {
+			visible = append(visible, event)
+		}
+	}
+	if len(visible) > 0 {
+		b.WriteString(labelStyle.Render("Timeline"))
+		b.WriteString("\n")
+		for _, event := range visible {
+			label, _ := event.DisplayLabel()
+			when := event.CreatedAt.Format("Jan 02 3:04 PM")
+			b.WriteString(valueStyle.Render(fmt.Sprintf("  %-20s %s", label, dimStyle.Render(when))))
+			b.WriteString("\n")
+		}
+		b.WriteString("\n")
+	}
+
+	// Shipping address
+	b.WriteString(labelStyle.Render("Ship To"))
+	b.WriteString("\n")
+	b.WriteString(valueStyle.Render("  " + order.ShippingName))
+	b.WriteString("\n")
+	b.WriteString(valueStyle.Render("  " + order.ShippingStreet))
+	b.WriteString("\n")
+	if order.ShippingStreet2 != "" {
+		b.WriteString(valueStyle.Render("  " + order.ShippingStreet2))
+		b.WriteString("\n")
+	}
+	cityLine := order.ShippingCity
+	if order.ShippingState != "" {
+		cityLine += ", " + order.ShippingState
+	}
+	cityLine += " " + order.ShippingZip
+	b.WriteString(valueStyle.Render("  " + cityLine))
+	b.WriteString("\n")
+	b.WriteString(valueStyle.Render("  " + order.ShippingCountry))
+	b.WriteString("\n\n")
+
+	// Footer hint
+	if order.CanRequestRefund() {
+		b.WriteString(dimStyle.Render("r: refund  esc: back to orders"))
+	} else {
+		b.WriteString(dimStyle.Render("esc: back to orders"))
+	}
+
+	return b.String()
+}
+
+// displayStyle maps a model-layer DisplayKind token to a themed lipgloss style.
+// Keeps pkg/models free of UI deps.
+func (m Model) displayStyle(k models.DisplayKind) lipgloss.Style {
+	switch k {
+	case models.DisplayKindSuccess:
+		return m.theme.TextSuccess()
+	case models.DisplayKindBrand:
+		return m.theme.TextBrand()
+	case models.DisplayKindAccent:
+		return m.theme.TextAccent()
+	case models.DisplayKindError:
+		return m.theme.TextError()
+	case models.DisplayKindWarning:
+		return m.theme.TextLoading()
+	case models.DisplayKindRefund:
+		return m.theme.TextBrand()
+	}
+	return m.theme.TextHighlight()
+}

pkg/tui/breadcrumbs.go

@@ -1,7 +1,7 @@
 package tui
 
 import (
-	"github.com/charmbracelet/lipgloss"
+	"charm.land/lipgloss/v2"
 )
 
 func (m Model) BuildBreadcrumbs() string {

pkg/tui/cart.go

@@ -3,41 +3,48 @@ package tui
 import (
 	"fmt"
 
-	"github.com/charmbracelet/bubbles/viewport"
-	tea "github.com/charmbracelet/bubbletea"
-	"github.com/charmbracelet/lipgloss"
+	"charm.land/bubbles/v2/viewport"
+	tea "charm.land/bubbletea/v2"
+	"charm.land/lipgloss/v2"
 )
 
 func (m Model) updateCartViewport() Model {
+	contentW, _, _, _ := m.shopLayout()
 	headerH := lipgloss.Height(m.BuildHeader())
 	breadH := lipgloss.Height(m.BuildBreadcrumbs())
 	footerH := lipgloss.Height(m.BuildFooter())
-	availH := m.heightContainer - headerH - footerH - breadH
+	// 2 = blank gap rows around the cart list
+	availH := m.heightContainer - headerH - footerH - breadH - 2
 	if availH < 1 {
 		availH = 1
 	}
 	if !m.cart.viewportReady {
-		m.cart.viewport = viewport.New(m.widthContent, availH)
+		m.cart.viewport = viewport.New(viewport.WithWidth(contentW), viewport.WithHeight(availH))
 		m.cart.viewport.KeyMap = viewport.KeyMap{}
 		m.cart.viewportReady = true
 	} else {
-		m.cart.viewport.Width = m.widthContent
-		m.cart.viewport.Height = availH
+		m.cart.viewport.SetWidth(contentW)
+		m.cart.viewport.SetHeight(availH)
 	}
 	return m
 }
 
 func (m Model) generateCartContent() string {
-	if len(m.Cart) == 0 {
+	contentW, _, _, _ := m.shopLayout()
+
+	if m.IsCartEmpty() {
 		emptyStyle := m.theme.TextDim().
 			Align(lipgloss.Center).
-			Width(m.widthContent).
+			Width(contentW).
 			Padding(2, 0)
-		return emptyStyle.Render("Your cart is empty\n\nPress s to go back to shop")
+		render := emptyStyle.Render("Your cart is empty\n\nPress s to go back to shop")
+		return render
 	}
 
 	cartItems := ""
-	boxWidth := m.widthContent - 4
+	// Cart cards span the full chrome width so they line up with the
+	// header and footer boxes.
+	boxWidth := contentW
 	itemSlice := m.GetCartItemsSlice()
 
 	boxPadding := 0
@@ -86,29 +93,14 @@ func (m Model) generateCartContent() string {
 
 		boxContent := contentLine1 + "\n" + contentLine2
 
-		var itemBox lipgloss.Style
-		if idx == m.cart.cursor {
-			itemBox = lipgloss.NewStyle().
-				Border(lipgloss.NormalBorder(), true).
-				BorderForeground(m.theme.Accent()).
-				Padding(boxPadding, 2).
-				Width(boxWidth).
-				Foreground(m.theme.Accent()).
-				Bold(true)
+		isSelected := idx == m.cart.cursor
+		if isSelected {
+			boxContent = m.theme.TextAccent().Bold(true).Render(boxContent)
 		} else {
-			itemBox = lipgloss.NewStyle().
-				Border(lipgloss.NormalBorder()).
-				BorderForeground(m.theme.Border()).
-				Padding(boxPadding, 2).
-				Width(boxWidth).
-				Foreground(m.theme.Accent())
+			boxContent = m.theme.TextAccent().Render(boxContent)
 		}
-
-		centered := lipgloss.NewStyle().
-			Width(m.widthContent).
-			Align(lipgloss.Center)
-
-		cartItems += centered.Render(itemBox.Render(boxContent))
+		box := m.createBoxInner(boxContent, isSelected, lipgloss.Left, 2, boxPadding, boxWidth)
+		cartItems += box
 
 		if idx < len(itemSlice)-1 {
 			cartItems += "\n"
@@ -124,21 +116,22 @@ func (m Model) CartView() string {
 	content := m.generateCartContent()
 	m.cart.viewport.SetContent(content)
 	if len(m.Cart) > 0 {
-		itemHeight := 5
+		boxPadding := 0
+		if m.heightContainer >= 25 {
+			boxPadding = 1
+		}
+		itemHeight := 4 + 2*boxPadding + 1
 		targetY := m.cart.cursor * itemHeight
-		if targetY < m.cart.viewport.YOffset {
+		if targetY < m.cart.viewport.YOffset() {
 			m.cart.viewport.SetYOffset(targetY)
 		}
-		if targetY+itemHeight > m.cart.viewport.YOffset+m.cart.viewport.Height {
-			m.cart.viewport.SetYOffset(targetY - m.cart.viewport.Height + itemHeight)
+		if targetY+itemHeight > m.cart.viewport.YOffset()+m.cart.viewport.Height() {
+			m.cart.viewport.SetYOffset(targetY - m.cart.viewport.Height() + itemHeight)
 		}
 	}
-	return lipgloss.Place(
-		m.widthContainer,
-		lipgloss.Height(m.cart.viewport.View()),
-		lipgloss.Center, lipgloss.Center,
-		m.cart.viewport.View(),
-	)
+	// Blank rows separate the list from the chrome; no Place wrapper so the
+	// cards stay left-aligned with the header and footer boxes.
+	return "\n" + m.cart.viewport.View() + "\n"
 }
 
 func (m Model) CartUpdate(msg tea.Msg) (Model, tea.Cmd) {
@@ -159,7 +152,8 @@ func (m Model) CartUpdate(msg tea.Msg) (Model, tea.Cmd) {
 		cartItems := m.GetCartItemsSlice()
 		if m.cart.cursor >= 0 && m.cart.cursor < len(cartItems) {
 			cartItems[m.cart.cursor].Quantity++
-			return m, m.syncCartItemCmd(cartItems[m.cart.cursor].CoffeeID, cartItems[m.cart.cursor].Quantity)
+			m, cmd := m.syncCartItemCmd(cartItems[m.cart.cursor].CoffeeID, cartItems[m.cart.cursor].Quantity)
+			return m, cmd
 		}
 	case "-", "_":
 		cartItems := m.GetCartItemsSlice()
@@ -176,10 +170,11 @@ func (m Model) CartUpdate(msg tea.Msg) (Model, tea.Cmd) {
 				}
 				newQty = 0
 			}
-			return m, m.syncCartItemCmd(coffeeID, newQty)
+			m, cmd := m.syncCartItemCmd(coffeeID, newQty)
+			return m, cmd
 		}
 	case "p", "enter":
-		if len(m.Cart) > 0 {
+		if !m.IsCartEmpty() {
 			return m.ShippingSwitch()
 		}
 	}

pkg/tui/confirmation.go

@@ -3,11 +3,13 @@ package tui
 import (
 	"fmt"
 	"strings"
-	"terminalShop/pkg/models"
 
-	"github.com/charmbracelet/bubbles/viewport"
-	tea "github.com/charmbracelet/bubbletea"
-	"github.com/charmbracelet/lipgloss"
+	"terminalShop/pkg/models"
+	"terminalShop/pkg/tui/qrfefe"
+
+	"charm.land/bubbles/v2/viewport"
+	tea "charm.land/bubbletea/v2"
+	"charm.land/lipgloss/v2"
 )
 
 // RenderConfirmation renders the order confirmation view
@@ -73,12 +75,12 @@ func (m Model) updateConfirmViewport() Model {
 		availH = 1
 	}
 	if !m.confirm.viewportReady {
-		m.confirm.viewport = viewport.New(m.widthContent, availH)
+		m.confirm.viewport = viewport.New(viewport.WithWidth(m.widthContent), viewport.WithHeight(availH))
 		m.confirm.viewport.KeyMap = viewport.DefaultKeyMap()
 		m.confirm.viewportReady = true
 	} else {
-		m.confirm.viewport.Width = m.widthContent
-		m.confirm.viewport.Height = availH
+		m.confirm.viewport.SetWidth(m.widthContent)
+		m.confirm.viewport.SetHeight(availH)
 	}
 	return m
 }
@@ -132,7 +134,11 @@ func (m Model) generateReviewContent() string {
 	view := strings.Builder{}
 
 	if m.review.cardJustAdded {
-		view.WriteString(m.theme.TextSuccess().Bold(true).Render("card added successfully") + "\n\n")
+		if m.review.cardWasDuplicate {
+			view.WriteString(m.theme.TextDim().Render("identical card already saved... using existing card") + "\n\n")
+		} else {
+			view.WriteString(m.theme.TextSuccess().Bold(true).Render("card added successfully") + "\n\n")
+		}
 	}
 
 	if m.ShippingInfo != nil {
@@ -141,23 +147,21 @@ func (m Model) generateReviewContent() string {
 		if m.ShippingInfo.Street2 != "" {
 			view.WriteString(m.ShippingInfo.Street2 + "\n")
 		}
-		view.WriteString(fmt.Sprintf("%s,  %s %s,  %s\n", m.ShippingInfo.City, m.ShippingInfo.State, m.ShippingInfo.Zip, m.ShippingInfo.Country))
+		fmt.Fprintf(&view, "%s,  %s %s,  %s\n", m.ShippingInfo.City, m.ShippingInfo.State, m.ShippingInfo.Zip, m.ShippingInfo.Country)
 	}
 	view.WriteString("\n")
 
 	if m.SelectedCard != nil {
-		view.WriteString(fmt.Sprintf("cc: **** **** **** %s\n", m.SelectedCard.Last4))
+		fmt.Fprintf(&view, "cc: **** **** **** %s\n", m.SelectedCard.Last4)
 	}
 	view.WriteString("\n")
 
-	subtotal := 0
-	for _, item := range m.GetCartItemsSlice() {
-		subtotal += item.Coffee.Price * item.Quantity
-	}
-	view.WriteString(fmt.Sprintf("subtotal: %s\n", formatUSD(subtotal)))
+	subtotal := m.CalculateSubtotal()
+
+	fmt.Fprintf(&view, "subtotal: %s\n", formatUSD(subtotal))
 	view.WriteString(m.theme.TextAccent().Render(fmt.Sprintf("total:    %s", formatUSD(subtotal))) + "\n")
 	view.WriteString("\n")
-	view.WriteString(m.theme.TextDim().Render("press enter to confirm") + "\n")
+	view.WriteString(m.theme.TextBrand().Render("press enter to confirm") + "\n")
 
 	return m.theme.Base().Padding(0, 1).Render(view.String())
 }
@@ -166,6 +170,30 @@ func (m Model) ReviewView() string {
 	if m.CheckingOut {
 		return m.theme.TextAccent().Bold(true).Padding(1).Render("  submitting order...")
 	}
+	if m.review.retrying {
+		return m.theme.TextAccent().Bold(true).Padding(1).Render("  retrying authentication...")
+	}
+	if m.review.retryExhausted {
+		content := m.theme.TextError().Bold(true).Padding(1).Render("too many authentication attempts") + "\n" + m.theme.TextLabel().Padding(0, 1).Render("press esc to start a new order")
+		return lipgloss.Place(
+			m.widthContainer,
+			lipgloss.Height(content),
+			lipgloss.Center, lipgloss.Center,
+			content,
+		)
+	}
+	if m.review.authFailed {
+		content := m.theme.TextError().Bold(true).Padding(1).Render("authentication failed — press r to retry, esc to go back")
+		return lipgloss.Place(
+			m.widthContainer,
+			lipgloss.Height(content),
+			lipgloss.Center, lipgloss.Center,
+			content,
+		)
+	}
+	if m.review.requiresAction {
+		return m.renderRequiresActionView()
+	}
 	if m.review.success {
 		content := m.theme.TextSuccess().Bold(true).Padding(1).Render("order placed successfully!")
 		return lipgloss.Place(
@@ -184,16 +212,50 @@ func (m Model) ReviewView() string {
 	)
 }
 
+// renderRequiresActionView shows a QR for the 3DS challenge URL while the TUI
+// polls the order status. Mirrors the add-card QR layout in payment_form.go.
+func (m Model) renderRequiresActionView() string {
+	base := m.theme.TextLabel()
+	accent := m.theme.TextHighlight()
+	header := m.theme.TextAccent().Bold(true).Render("your bank wants to verify this charge")
+
+	if m.review.redirectURL == "" {
+		return base.Render("  verifying with your bank...")
+	}
+
+	qr, qrSize, err := qrfefe.Generate(m.review.redirectURL)
+	if err != nil || qrSize > m.widthContent {
+		body := header + "\n\n" +
+			base.Render("open this url on your phone to authenticate:") + "\n\n" +
+			accent.Render(m.review.redirectURL) + "\n\n" +
+			base.Render("waiting for completion...")
+		return lipgloss.Place(m.widthContainer, lipgloss.Height(body), lipgloss.Center, lipgloss.Center, body)
+	}
+
+	// Same gotcha as payment_form.go: lipgloss layout helpers corrupt qrfefe ANSI.
+	return qr +
+		header + "\n" +
+		base.Render("scan or visit to complete authentication") + "\n" +
+		accent.Render(m.review.redirectURL) + "\n\n" +
+		base.Render("waiting for completion...")
+}
+
 func (m Model) ReviewUpdate(msg tea.Msg) (Model, tea.Cmd) {
 	switch msg := msg.(type) {
 	case CheckoutResultMsg:
 		m.CheckingOut = false
 		if msg.Err != nil {
-			m.ErrorMsg = fmt.Sprintf("checkout failed: %v", msg.Err)
-			m = m.SwitchPage(paymentPage)
-			m.payment.view = 0
-			m.payment.form = nil
-			return m, nil
+			var cmd tea.Cmd
+			m, cmd = m.switchForCheckoutError(msg.Err)
+			m.error = &VisibleError{message: friendlyCheckoutError(msg.Err)}
+			m.review.cardJustAdded = false
+			return m, cmd
+		}
+		if msg.RequiresAction {
+			m.review.requiresAction = true
+			m.review.redirectURL = msg.RedirectURL
+			m.review.orderID = msg.OrderID
+			return m, m.schedulePollOrderStatus(msg.OrderID)
 		}
 		m.Cart = make(map[uint]*models.CartItem)
 		m.cart.cursor = 0
@@ -202,13 +264,121 @@ func (m Model) ReviewUpdate(msg tea.Msg) (Model, tea.Cmd) {
 		m.review.success = true
 		return m, nil
 
+	case OrderStatusMsg:
+		if !m.review.requiresAction || msg.OrderID != m.review.orderID {
+			return m, nil
+		}
+		if msg.Err != nil {
+			// Transient — keep polling.
+			return m, m.schedulePollOrderStatus(msg.OrderID)
+		}
+		switch msg.Status {
+		case "paid", "shipped", "delivered":
+			m.Cart = make(map[uint]*models.CartItem)
+			m.cart.cursor = 0
+			m.ShippingInfo = nil
+			m.OrdersLoaded = false
+			m.review.requiresAction = false
+			m.review.redirectURL = ""
+			m.review.success = true
+			return m, nil
+		case "failed", "cancelled":
+			m.review.requiresAction = false
+			m.review.redirectURL = ""
+			m.review.authFailed = true
+			m.footer = []footerCommand{{key: "r", value: "retry"}, {key: "esc", value: "back"}}
+			return m, nil
+		default:
+			return m, m.schedulePollOrderStatus(msg.OrderID)
+		}
+
+	case RetryAuthResultMsg:
+		if m.review.orderID != 0 && msg.OrderID != m.review.orderID {
+			return m, nil
+		}
+		m.review.retrying = false
+		if msg.Err != nil {
+			s := msg.Err.Error()
+			switch {
+			case strings.Contains(s, "RETRY_LIMIT"):
+				m.review.authFailed = false
+				m.review.retryExhausted = true
+				m.footer = []footerCommand{{key: "esc", value: "back"}}
+				return m, nil
+			case strings.Contains(s, "CARD_NO_LONGER_AVAILABLE"):
+				m.review.authFailed = false
+				m.review.requiresAction = false
+				m.review.redirectURL = ""
+				m.review.orderID = 0
+				m = m.SwitchPage(paymentPage)
+				m.payment.view = 0
+				m.payment.form = nil
+				m.error = &VisibleError{message: "saved card is no longer available. add it again to try."}
+				return m, nil
+			default:
+				m.error = &VisibleError{message: friendlyCheckoutError(msg.Err)}
+				return m, nil
+			}
+		}
+		m.review.authFailed = false
+		m.review.retryExhausted = false
+		m.review.requiresAction = true
+		m.review.redirectURL = msg.RedirectURL
+		m.review.orderID = msg.OrderID
+		m.footer = []footerCommand{{key: "esc", value: "cancel"}}
+		return m, m.schedulePollOrderStatus(msg.OrderID)
+
 	case tea.KeyMsg:
 		if m.CheckingOut {
 			return m, nil
 		}
+		if m.review.retrying {
+			return m, nil
+		}
+		if m.review.authFailed {
+			switch msg.String() {
+			case "r":
+				if m.review.orderID == 0 {
+					return m, nil
+				}
+				m.review.retrying = true
+				m.error = nil
+				return m, m.retryAuthCmd(m.review.orderID)
+			case "esc":
+				m.review.authFailed = false
+				m = m.SwitchPage(paymentPage)
+				m.payment.view = 0
+				m.payment.form = nil
+				return m, nil
+			}
+			return m, nil
+		}
+		if m.review.retryExhausted {
+			if msg.String() == "esc" {
+				m.review.retryExhausted = false
+				m.review.orderID = 0
+				m = m.SwitchPage(paymentPage)
+				m.payment.view = 0
+				m.payment.form = nil
+				return m, nil
+			}
+			return m, nil
+		}
+		if m.review.requiresAction {
+			if msg.String() == "esc" {
+				m.review.requiresAction = false
+				m.review.redirectURL = ""
+				m = m.SwitchPage(paymentPage)
+				m.payment.view = 0
+				return m, nil
+			}
+			return m, nil
+		}
 		if m.review.success {
 			m.review.success = false
 			m.review.cardJustAdded = false
+			m.shipping.form = nil
+			m.payment.form = nil
 			m, _ = m.ShopSwitch()
 			return m, func() tea.Msg {
 				if m.APIClient != nil {
@@ -229,3 +399,40 @@ func (m Model) ReviewUpdate(msg tea.Msg) (Model, tea.Cmd) {
 	}
 	return m, nil
 }
+
+func (m Model) switchForCheckoutError(err error) (Model, tea.Cmd) {
+	switch {
+	case strings.Contains(err.Error(), "CART_OVER_LIMIT"):
+		return m.CartSwitch()
+	default:
+		m = m.SwitchPage(paymentPage)
+		m.payment.view = 0
+		m.payment.form = nil
+		return m, nil
+	}
+}
+
+func friendlyCheckoutError(raw error) string {
+	s := raw.Error()
+	switch {
+	case strings.Contains(s, "CART_OVER_LIMIT"):
+		return "order total is over the per-order limit. remove items and try again."
+	case strings.Contains(s, "AUTHENTICATION_REQUIRED"):
+		return "your bank wants to verify this charge, authentication step coming soon."
+	case strings.Contains(s, "AUTHENTICATION_NOT_SUPPORTED"):
+		return "this card doesn't support online authentication. Try another card"
+	case strings.Contains(s, "CARD_STORAGE_EXPIRED"):
+		return "saved card expired. Add it again to verify the card is still yours"
+	case strings.Contains(s, "CARD_EXPIRED"):
+		return "card expired. Add a new card and try again"
+	case strings.Contains(s, "CARD_CVC_FAILED"):
+		return "card cvc incorrect. Check the back of the card and try again"
+	case strings.Contains(s, "CARD_INSUFFICIENT_FUNDS"):
+		return "insufficient funds on this card"
+	case strings.Contains(s, "CARD_PROCESSING_ERROR"):
+		return "card processing error. Try again in a moment"
+	case strings.Contains(s, "CARD_DECLINED"):
+		return "card declined"
+	}
+	return "checkout failed, try again."
+}

pkg/tui/confirmation_retry_test.go

@@ -0,0 +1,394 @@
+package tui
+
+import (
+	"errors"
+	"strings"
+	"testing"
+
+	tea "charm.land/bubbletea/v2"
+)
+
+// newReviewModel returns a Model sitting on the review page with the default
+// layout already applied. Use as the starting point for every retry-auth
+// state machine test so transitions assert from a realistic baseline.
+func newReviewModel(t *testing.T) Model {
+	t.Helper()
+	m := NewModel("test")
+	m.currentPage = reviewPage
+	return m
+}
+
+// keyR / keyEsc / keyJ build the bubbletea v2 key events Update expects.
+// KeyMsg is an interface; KeyPressMsg satisfies it. Key.String() returns
+// Text when non-empty, otherwise the keystroke (which is why esc relies on
+// Code: tea.KeyEsc rather than Text).
+func keyR() tea.KeyMsg   { return tea.KeyPressMsg{Text: "r", Code: 'r'} }
+func keyEsc() tea.KeyMsg { return tea.KeyPressMsg{Code: tea.KeyEsc} }
+func keyJ() tea.KeyMsg   { return tea.KeyPressMsg{Text: "j", Code: 'j'} }
+
+func TestRetryAuthCmd_NilClient(t *testing.T) {
+	m := NewModel("test")
+	m.APIClient = nil
+	cmd := m.retryAuthCmd(42)
+	if cmd == nil {
+		t.Fatal("retryAuthCmd returned nil cmd")
+	}
+	msg := cmd()
+	rm, ok := msg.(RetryAuthResultMsg)
+	if !ok {
+		t.Fatalf("expected RetryAuthResultMsg, got %T", msg)
+	}
+	if rm.OrderID != 42 {
+		t.Errorf("OrderID = %d, want 42", rm.OrderID)
+	}
+	if rm.Err == nil || !strings.Contains(rm.Err.Error(), "api client unavailable") {
+		t.Errorf("expected api-client-unavailable err, got %v", rm.Err)
+	}
+}
+
+func TestReviewView_RetryingShowsCopy(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	out := m.ReviewView()
+	if !strings.Contains(out, "retrying authentication") {
+		t.Fatalf("missing retrying copy in: %q", out)
+	}
+}
+
+func TestReviewView_RetryExhaustedShowsCopy(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retryExhausted = true
+	out := m.ReviewView()
+	if !strings.Contains(out, "too many authentication attempts") {
+		t.Fatalf("missing retry-exhausted copy in: %q", out)
+	}
+	if !strings.Contains(out, "press esc to start a new order") {
+		t.Fatalf("missing recovery hint in: %q", out)
+	}
+}
+
+func TestReviewView_AuthFailedAdvertisesRetry(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.authFailed = true
+	out := m.ReviewView()
+	if !strings.Contains(out, "press r to retry") {
+		t.Fatalf("authFailed copy must advertise r: %q", out)
+	}
+	if !strings.Contains(out, "esc to go back") {
+		t.Fatalf("authFailed copy must advertise esc: %q", out)
+	}
+}
+
+func TestRenderRequiresActionView_FrictionlessShowsVerifying(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.requiresAction = true
+	m.review.redirectURL = ""
+	out := m.renderRequiresActionView()
+	if !strings.Contains(out, "verifying with your bank") {
+		t.Fatalf("frictionless retry-success path must show verifying copy: %q", out)
+	}
+}
+
+func TestReviewUpdate_AuthFailed_PressR_StartsRetry(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.authFailed = true
+	m.review.orderID = 7
+	m.error = &VisibleError{message: "leftover banner"}
+
+	out, cmd := m.ReviewUpdate(keyR())
+	if !out.review.retrying {
+		t.Fatal("expected retrying=true after r press")
+	}
+	if out.error != nil {
+		t.Fatal("stale banner should be cleared when retry starts")
+	}
+	if cmd == nil {
+		t.Fatal("expected non-nil cmd to call retryAuth")
+	}
+}
+
+func TestReviewUpdate_AuthFailed_PressR_ZeroOrderID_NoOp(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.authFailed = true
+	m.review.orderID = 0
+
+	out, cmd := m.ReviewUpdate(keyR())
+	if out.review.retrying {
+		t.Fatal("retry must not start without an order id")
+	}
+	if cmd != nil {
+		t.Fatal("expected nil cmd when orderID=0")
+	}
+}
+
+func TestReviewUpdate_AuthFailed_PressEsc_BouncesToPayment(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, _ := m.ReviewUpdate(keyEsc())
+	if out.review.authFailed {
+		t.Fatal("authFailed must clear on esc")
+	}
+	if out.currentPage != paymentPage {
+		t.Fatalf("currentPage = %v, want paymentPage", out.currentPage)
+	}
+}
+
+func TestReviewUpdate_AuthFailed_OtherKey_NoOp(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, cmd := m.ReviewUpdate(keyJ())
+	if !out.review.authFailed {
+		t.Fatal("unrelated key must not clear authFailed")
+	}
+	if out.review.retrying {
+		t.Fatal("unrelated key must not start retry")
+	}
+	if cmd != nil {
+		t.Fatal("unrelated key must not produce a cmd")
+	}
+}
+
+func TestReviewUpdate_Retrying_BlocksKeys(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, cmd := m.ReviewUpdate(keyR())
+	if !out.review.retrying {
+		t.Fatal("retrying flag should persist while a retry is in flight")
+	}
+	if cmd != nil {
+		t.Fatal("r press while retrying must not spawn a second cmd")
+	}
+
+	out, cmd = m.ReviewUpdate(keyEsc())
+	if out.currentPage != reviewPage {
+		t.Fatalf("currentPage changed while retrying: %v", out.currentPage)
+	}
+	if cmd != nil {
+		t.Fatal("esc while retrying must not navigate away")
+	}
+}
+
+func TestReviewUpdate_RetryAuthResult_RequiresAction(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, cmd := m.ReviewUpdate(RetryAuthResultMsg{
+		OrderID:     7,
+		Status:      "requires_action",
+		RedirectURL: "https://stripe/auth/abc",
+	})
+
+	if out.review.retrying {
+		t.Fatal("retrying must clear when the result arrives")
+	}
+	if out.review.authFailed {
+		t.Fatal("authFailed must clear on retry success")
+	}
+	if !out.review.requiresAction {
+		t.Fatal("expected requiresAction=true so the QR view renders")
+	}
+	if out.review.redirectURL != "https://stripe/auth/abc" {
+		t.Fatalf("redirectURL = %q", out.review.redirectURL)
+	}
+	if cmd == nil {
+		t.Fatal("expected schedulePollOrderStatus cmd")
+	}
+	if len(out.footer) != 1 || out.footer[0].key != "esc" || out.footer[0].value != "cancel" {
+		t.Fatalf("footer = %+v, want only esc=cancel", out.footer)
+	}
+}
+
+func TestReviewUpdate_RetryAuthResult_FrictionlessSuccess(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	m.review.authFailed = true
+	m.review.orderID = 9
+
+	out, cmd := m.ReviewUpdate(RetryAuthResultMsg{
+		OrderID: 9,
+		Status:  "succeeded",
+	})
+
+	if !out.review.requiresAction {
+		t.Fatal("frictionless retry must set requiresAction=true to render the verifying view")
+	}
+	if out.review.redirectURL != "" {
+		t.Fatalf("redirectURL must stay empty for frictionless retry, got %q", out.review.redirectURL)
+	}
+	if cmd == nil {
+		t.Fatal("expected poll cmd to wait for the webhook")
+	}
+}
+
+func TestReviewUpdate_RetryAuthResult_RetryLimit(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, cmd := m.ReviewUpdate(RetryAuthResultMsg{
+		OrderID: 7,
+		Err:     errors.New("RETRY_LIMIT: too many authentication attempts, please use a different card"),
+	})
+
+	if out.review.retrying {
+		t.Fatal("retrying must clear after a result")
+	}
+	if !out.review.retryExhausted {
+		t.Fatal("expected retryExhausted=true on RETRY_LIMIT")
+	}
+	if out.review.authFailed {
+		t.Fatal("authFailed must clear when retryExhausted takes over")
+	}
+	if cmd != nil {
+		t.Fatal("RETRY_LIMIT is terminal — no follow-up cmd")
+	}
+	if len(out.footer) != 1 || out.footer[0].key != "esc" {
+		t.Fatalf("footer = %+v, want only esc=back", out.footer)
+	}
+}
+
+func TestReviewUpdate_RetryAuthResult_CardGone(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, _ := m.ReviewUpdate(RetryAuthResultMsg{
+		OrderID: 7,
+		Err:     errors.New("CARD_NO_LONGER_AVAILABLE: saved card is no longer available, add it again to retry"),
+	})
+
+	if out.currentPage != paymentPage {
+		t.Fatalf("currentPage = %v, want paymentPage", out.currentPage)
+	}
+	if out.review.authFailed || out.review.requiresAction {
+		t.Fatal("auth state must reset when bouncing to payment")
+	}
+	if out.review.orderID != 0 {
+		t.Fatalf("orderID should reset to 0, got %d", out.review.orderID)
+	}
+	if out.error == nil || !strings.Contains(out.error.message, "saved card is no longer available") {
+		t.Fatalf("error banner missing or wrong copy: %+v", out.error)
+	}
+}
+
+func TestReviewUpdate_RetryAuthResult_Transient(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, cmd := m.ReviewUpdate(RetryAuthResultMsg{
+		OrderID: 7,
+		Err:     errors.New("CARD_DECLINED: card declined"),
+	})
+
+	if out.review.retrying {
+		t.Fatal("retrying must clear after a result")
+	}
+	if !out.review.authFailed {
+		t.Fatal("authFailed must persist so the user can retry again")
+	}
+	if out.review.retryExhausted {
+		t.Fatal("transient errors must not flip retryExhausted")
+	}
+	if out.error == nil {
+		t.Fatal("expected friendly banner for transient error")
+	}
+	if cmd != nil {
+		t.Fatal("transient error must not start a poll")
+	}
+}
+
+func TestReviewUpdate_RetryAuthResult_OrderIDMismatch(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retrying = true
+	m.review.authFailed = true
+	m.review.orderID = 7
+
+	out, cmd := m.ReviewUpdate(RetryAuthResultMsg{
+		OrderID:     99,
+		Status:      "requires_action",
+		RedirectURL: "https://wrong",
+	})
+
+	if !out.review.retrying {
+		t.Fatal("mismatched orderID must leave retrying unchanged")
+	}
+	if out.review.requiresAction {
+		t.Fatal("mismatched orderID must not flip requiresAction")
+	}
+	if out.review.redirectURL == "https://wrong" {
+		t.Fatal("mismatched orderID must not adopt the foreign URL")
+	}
+	if cmd != nil {
+		t.Fatal("mismatched orderID must not start a poll")
+	}
+}
+
+func TestReviewUpdate_RetryExhausted_PressEsc_BouncesToPayment(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retryExhausted = true
+	m.review.orderID = 7
+
+	out, _ := m.ReviewUpdate(keyEsc())
+	if out.review.retryExhausted {
+		t.Fatal("retryExhausted must clear on esc")
+	}
+	if out.review.orderID != 0 {
+		t.Fatalf("orderID should reset to 0, got %d", out.review.orderID)
+	}
+	if out.currentPage != paymentPage {
+		t.Fatalf("currentPage = %v, want paymentPage", out.currentPage)
+	}
+}
+
+func TestReviewUpdate_RetryExhausted_OtherKey_NoOp(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.retryExhausted = true
+
+	out, cmd := m.ReviewUpdate(keyR())
+	if !out.review.retryExhausted {
+		t.Fatal("unrelated key must not clear retryExhausted")
+	}
+	if cmd != nil {
+		t.Fatal("unrelated key must not produce a cmd")
+	}
+}
+
+func TestReviewUpdate_OrderStatusFailed_SetsRetryFooter(t *testing.T) {
+	m := newReviewModel(t)
+	m.review.requiresAction = true
+	m.review.orderID = 7
+
+	out, _ := m.ReviewUpdate(OrderStatusMsg{OrderID: 7, Status: "failed"})
+
+	if !out.review.authFailed {
+		t.Fatal("expected authFailed=true after failed status")
+	}
+	if out.review.requiresAction {
+		t.Fatal("requiresAction must clear when poll resolves to failed")
+	}
+	hasR, hasEsc := false, false
+	for _, c := range out.footer {
+		if c.key == "r" && c.value == "retry" {
+			hasR = true
+		}
+		if c.key == "esc" && c.value == "back" {
+			hasEsc = true
+		}
+	}
+	if !hasR || !hasEsc {
+		t.Fatalf("footer missing r/esc retry hints: %+v", out.footer)
+	}
+}

pkg/tui/confirmation_test.go

@@ -0,0 +1,24 @@
+package tui
+
+import (
+	"errors"
+	"strings"
+	"testing"
+)
+
+func TestFriendlyCheckoutError_CardStorageExpired(t *testing.T) {
+	got := friendlyCheckoutError(errors.New("CARD_STORAGE_EXPIRED: saved card epired, add it again"))
+	if !strings.Contains(got, "saved card expired") {
+		t.Fatalf("want saved-card-expired copy, got %q", got)
+	}
+	if strings.Contains(got, "card expired. Add a new card") {
+		t.Fatalf("CARD_STORAGE_EXPIRED was matched by the CARD_EXPIRED branch: %q", got)
+	}
+}
+
+func TestFriendlyCheckoutError_CardExpiredStillReachable(t *testing.T) {
+	got := friendlyCheckoutError(errors.New("CARD_EXPIRED: card expired"))
+	if !strings.Contains(got, "card expired. Add a new card") {
+		t.Fatalf("want plain card-expired copy, got %q", got)
+	}
+}

pkg/tui/doc.go

@@ -0,0 +1,3 @@
+// Package tui is the terminal UI you see over SSH: the shop, the cart, your
+// account, and the checkout flow, all drawn with Bubbletea.
+package tui

pkg/tui/faq.json

@@ -1,50 +1,10 @@
 [
   {
-    "question": "help, i have a question about my order!",
-    "answer": "send us an email at support@terminal.shop."
+    "question": "i have a question!",
+    "answer": "I'm happy to answer any question! From questions about your order, to questions about working on the code, please contact me through my github @marcusDenslow, or at my email. marcus.allen.denslow@gmail.com"
   },
   {
-    "question": "when was my coffee roasted? the roast date is blank on my bag.",
-    "answer": "we roast your coffee within 24 hours of shipping, and you'll receive an email once your order ships. we're working on a solution to stamping the roast date on the bags, but so far all attempts have failed (the ink wipes off)."
-  },
-  {
-    "question": "where do you ship?",
-    "answer": "we ship all of our blends in the US. Unfortunately, we don't ship to other countries at this time. We are actively looking for other small-batch roasters in other countries and regions though!"
-  },
-  {
-    "question": "is your coffee ethically sourced?",
-    "answer": "absolutely."
-  },
-  {
-    "question": "is ordering via ssh secure?",
-    "answer": "you bet it is. arguably more secure than your browser. ssh incorporates encryption and authentication via a process called public key cryptography. if that doesn't sound secure we don't know what does."
-  },
-  {
-    "question": "what is cron?",
-    "answer": "cron is our monthly membership, available only in the US (for now). if you subscribe, you'll receive a new coffee blend every month, along with other surprises both physical and digital."
-  },
-  {
-    "question": "i tried to subscribe to cron, but it says i need a public key?",
-    "answer": "we don't allow subscriptions without a public key, as you won't be able to ssh back in with the same identity (we treat users without a public key as anonymous). create a key with `ssh-keygen -t rsa` and make sure your ssh client isn't omitting your key."
-  },
-  {
-    "question": "how do you store my data?",
-    "answer": "we store minimal information about you when you order through our ssh shop: name, shipping address and email, along with a fingerprint generated from your public key. all payment information is stored exclusively by Stripe."
-  },
-  {
-    "question": "do you offer a subscription?",
-    "answer": "in addition to cron, our monthly membership, you can also subscribe to any of the blends offered in our shop."
-  },
-  {
-    "question": "will Terminal coffee make me a better developer?",
-    "answer": "legally we cannot guarantee that it will, but..."
-  },
-  {
-    "question": "does coffee from the command line taste better than regular coffee?",
-    "answer": "it's just science!"
-  },
-  {
-    "question": "is it true your coffee contains the tears of @thdxr?",
-    "answer": "yes, this is true."
+		"question": "why is it so empty here?",
+		"answer": "more is to come!"
   }
 ]

pkg/tui/footer.go

@@ -1,194 +1,31 @@
 package tui
 
 import (
-	"fmt"
+	"strings"
 
-	"github.com/charmbracelet/lipgloss"
+	"charm.land/lipgloss/v2"
 )
 
+// BuildFooter renders the bottom chrome bar with the current page keybinds.
+// Layout ported from the design prototype at ~/programming/test/shop.go.
 func (m Model) BuildFooter() string {
-	// Style for keybinds (bold)
-	keybindStyle := m.theme.TextDim().Bold(true)
+	_, _, _, wideW := m.shopLayout()
 
-	// Style for descriptions (normal)
-	descStyle := m.theme.TextDim()
+	item := func(k, v string) string {
+		return pBody.Render(k) + " " + pDim.Render(v)
+	}
 
-	// On small terminals, only show the menu hint
+	var keys string
 	if m.size == small {
-		footerText := keybindStyle.Render("m") + " " + descStyle.Render("menu")
-		return lipgloss.NewStyle().Align(lipgloss.Center).Width(m.widthContainer).Render(footerText)
-	}
-
-	var footerText string
-	if m.account.faqFocused {
-		footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s    %s %s",
-			keybindStyle.Render("j/k"),
-			descStyle.Render("scroll"),
-			keybindStyle.Render("esc"),
-			descStyle.Render("back"),
-			keybindStyle.Render("s"),
-			descStyle.Render("shop"),
-			keybindStyle.Render("c"),
-			descStyle.Render("cart"),
-			keybindStyle.Render("q"),
-			descStyle.Render("quit"),
-		)
-	} else if m.currentPage == accountPage {
-		switch m.account.orderViewState {
-		case 2:
-			// Viewing single order detail
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s",
-				keybindStyle.Render("esc"),
-				descStyle.Render("back"),
-				keybindStyle.Render("s"),
-				descStyle.Render("shop"),
-				keybindStyle.Render("q"),
-				descStyle.Render("quit"),
-			)
-		case 1:
-			// Browsing order list
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s",
-				keybindStyle.Render("j/k"),
-				descStyle.Render("orders"),
-				keybindStyle.Render("enter"),
-				descStyle.Render("details"),
-				keybindStyle.Render("esc"),
-				descStyle.Render("back"),
-				keybindStyle.Render("q"),
-				descStyle.Render("quit"),
-			)
-		default:
-			// Account tabs
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s    %s %s    %s %s",
-				keybindStyle.Render("j/k"),
-				descStyle.Render("navigate"),
-				keybindStyle.Render("enter"),
-				descStyle.Render("select"),
-				keybindStyle.Render("s"),
-				descStyle.Render("shop"),
-				keybindStyle.Render("c"),
-				descStyle.Render("cart"),
-				keybindStyle.Render("?"),
-				descStyle.Render("help"),
-				keybindStyle.Render("q"),
-				descStyle.Render("quit"),
-			)
-		}
-	} else if m.currentPage == confirmPage {
-		// Confirmation screen
-		footerText = fmt.Sprintf("%s %s    %s %s",
-			keybindStyle.Render("esc"),
-			descStyle.Render("back to shop"),
-			keybindStyle.Render("q"),
-			descStyle.Render("quit"),
-		)
-	} else if m.currentPage == shippingPage {
-		if m.shipping.view == 0 && m.shipping.form == nil {
-			// Address list
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s",
-				keybindStyle.Render("j/k"),
-				descStyle.Render("addresses"),
-				keybindStyle.Render("enter"),
-				descStyle.Render("select"),
-				keybindStyle.Render("d/x"),
-				descStyle.Render("delete"),
-				keybindStyle.Render("esc"),
-				descStyle.Render("back"),
-			)
-		} else {
-			// Shipping form
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s",
-				keybindStyle.Render("tab"),
-				descStyle.Render("next"),
-				keybindStyle.Render("enter"),
-				descStyle.Render("submit"),
-				keybindStyle.Render("esc"),
-				descStyle.Render("back"),
-			)
-		}
-	} else if m.currentPage == paymentPage {
-		if m.payment.view == 0 && m.payment.form == nil {
-			// Card list
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s",
-				keybindStyle.Render("j/k"),
-				descStyle.Render("cards"),
-				keybindStyle.Render("enter"),
-				descStyle.Render("select"),
-				keybindStyle.Render("d/x"),
-				descStyle.Render("delete"),
-				keybindStyle.Render("esc"),
-				descStyle.Render("back"),
-			)
-		} else if m.CheckingOut {
-			// Submitting order
-			footerText = descStyle.Render("submitting order...")
-		} else {
-			// Payment form
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s",
-				keybindStyle.Render("tab"),
-				descStyle.Render("next"),
-				keybindStyle.Render("enter"),
-				descStyle.Render("submit"),
-				keybindStyle.Render("esc"),
-				descStyle.Render("back"),
-			)
-		}
-	} else if m.currentPage == cartPage {
-		// In cart view, show proceed option
-		if len(m.Cart) > 0 {
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s    %s %s    %s %s    %s %s    %s %s",
-				keybindStyle.Render("j/k"),
-				descStyle.Render("items"),
-				keybindStyle.Render("+/-"),
-				descStyle.Render("qty"),
-				keybindStyle.Render("p/enter"),
-				descStyle.Render("checkout"),
-				keybindStyle.Render("s"),
-				descStyle.Render("shop"),
-				keybindStyle.Render("a"),
-				descStyle.Render("account"),
-				keybindStyle.Render("pgup/pgdn"),
-				descStyle.Render("scroll"),
-				keybindStyle.Render("?"),
-				descStyle.Render("help"),
-				keybindStyle.Render("q"),
-				descStyle.Render("quit"),
-			)
-		} else {
-			footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s    %s %s    %s %s",
-				keybindStyle.Render("j/k"),
-				descStyle.Render("items"),
-				keybindStyle.Render("+/-"),
-				descStyle.Render("qty"),
-				keybindStyle.Render("s"),
-				descStyle.Render("shop"),
-				keybindStyle.Render("a"),
-				descStyle.Render("account"),
-				keybindStyle.Render("?"),
-				descStyle.Render("help"),
-				keybindStyle.Render("q"),
-				descStyle.Render("quit"),
-			)
-		}
+		keys = item("m", "menu")
 	} else {
-		footerText = fmt.Sprintf("%s %s    %s %s    %s %s    %s %s    %s %s    %s %s",
-			keybindStyle.Render("j/k"),
-			descStyle.Render("products"),
-			keybindStyle.Render("+/-"),
-			descStyle.Render("qty"),
-			keybindStyle.Render("c"),
-			descStyle.Render("cart"),
-			keybindStyle.Render("a"),
-			descStyle.Render("account"),
-			keybindStyle.Render("?"),
-			descStyle.Render("help"),
-			keybindStyle.Render("q"),
-			descStyle.Render("quit"),
-		)
+		parts := make([]string, 0, len(m.footer))
+		for _, cmd := range m.footer {
+			parts = append(parts, item(cmd.key, cmd.value))
+		}
+		keys = strings.Join(parts, pDim.Render(" · "))
 	}
 
-	return lipgloss.NewStyle().
-		Align(lipgloss.Center).
-		Width(m.widthContainer).
-		Render(footerText)
+	row := lipgloss.NewStyle().Width(wideW).Align(lipgloss.Center).Render(keys)
+	return panel(wideW, 0, row)
 }

pkg/tui/header.go

@@ -2,91 +2,72 @@ package tui
 
 import (
 	"fmt"
+	"image/color"
+	"strings"
 
-	"github.com/charmbracelet/lipgloss"
+	"charm.land/lipgloss/v2"
 )
 
-func (m Model) BuildHeader() string {
-	// Calculate cart total and item count
-	total := 0
-	itemCount := 0
+// cartBlendColor mixes the colors of all cart items, weighted by quantity,
+// so the header price tints toward whatever dominates the cart.
+func (m Model) cartBlendColor() color.Color {
+	var rSum, gSum, bSum, n int
 	for _, item := range m.Cart {
-		total += item.Quantity * item.Coffee.Price
-		itemCount += item.Quantity
-	}
-
-	// Define colors
-	grayStyle := m.theme.TextBody()
-	boldWhiteStyle := m.theme.TextAccent().Bold(true)
-	boldGrayStyle := m.theme.TextBody().Bold(true)
-
-	// Build cart tab (used in all sizes)
-	itemCountText := grayStyle.Render(fmt.Sprintf("[%d]", itemCount))
-
-	var cartKeybind, cartName, cartInfo string
-	if m.inCartFlow() {
-		// Active: bold white keybind and name
-		cartKeybind = boldWhiteStyle.Render("c")
-		cartName = boldWhiteStyle.Render("cart")
-		cartInfo = fmt.Sprintf(" %s %s",
-			boldWhiteStyle.Render(fmt.Sprintf("$%.2f", float64(total)/100)),
-			itemCountText)
-	} else {
-		// Inactive: bold gray keybind, gray name
-		cartKeybind = boldGrayStyle.Render("c")
-		cartName = grayStyle.Render("cart")
-		cartInfo = fmt.Sprintf(" %s %s",
-			boldWhiteStyle.Render(fmt.Sprintf("$%.2f", float64(total)/100)),
-			itemCountText)
-	}
-	cartTab := cartKeybind + " " + cartName + cartInfo
-
-	var tabsContent string
-
-	switch m.size {
-	case small:
-		// Small: just a mark + Cart
-		mark := boldWhiteStyle.Render("t")
-		tabsContent = mark + "    " + cartTab
-	case medium:
-		menuTab := boldGrayStyle.Render("m") + " " + grayStyle.Render("menu")
-		logo := boldWhiteStyle.Render("terminal coffee")
-		separator := m.theme.TextAccent().Render("|")
-		tabsContent = menuTab + " " + separator + " " + logo + " " + separator + " " + cartTab
-	default:
-		separator := m.theme.TextAccent().Render("|")
-
-		var shopKeybind, shopName string
-		if m.currentPage == shopPage {
-			shopKeybind = boldWhiteStyle.Render("s")
-			shopName = boldWhiteStyle.Render("shop")
-		} else {
-			shopKeybind = boldGrayStyle.Render("s")
-			shopName = grayStyle.Render("shop")
+		r, g, b, ok := parseHexColor(item.Coffee.Color)
+		if !ok {
+			continue
 		}
-
-		var accountKeybind, accountName string
-		if m.currentPage == accountPage {
-			accountKeybind = boldWhiteStyle.Render("a")
-			accountName = boldWhiteStyle.Render("account")
-		} else {
-			accountKeybind = boldGrayStyle.Render("a")
-			accountName = grayStyle.Render("account")
-		}
-
-		tabsContent = fmt.Sprintf("%s %s %s %s %s %s %s", shopKeybind, shopName, separator, accountKeybind, accountName, separator, cartTab)
+		rSum += r * item.Quantity
+		gSum += g * item.Quantity
+		bSum += b * item.Quantity
+		n += item.Quantity
 	}
-
-	// Add box with padding (no vertical padding, just horizontal)
-	tabBox := lipgloss.NewStyle().
-		Border(lipgloss.NormalBorder()).
-		Padding(0, 2).
-		MarginBottom(1)
-
-	// Center the whole thing within the container
-	centered := lipgloss.NewStyle().
-		Width(m.widthContainer).
-		Align(lipgloss.Center)
-
-	return centered.Render(tabBox.Render(tabsContent))
+	if n == 0 {
+		return cWhite
+	}
+	return lipgloss.Color(fmt.Sprintf("#%02X%02X%02X", rSum/n, gSum/n, bSum/n))
+}
+
+// BuildHeader renders the top chrome bar: brand, tab pills, and cart summary.
+// Layout ported from the design prototype at ~/programming/test/shop.go.
+func (m Model) BuildHeader() string {
+	_, _, _, wideW := m.shopLayout()
+
+	brand := pWht.Bold(true).Render("terminal")
+
+	pill := lipgloss.NewStyle().Background(cPill).Foreground(cWhite).Bold(true).Padding(0, 1)
+	tab := func(key, label string, active bool) string {
+		if active {
+			return pill.Render(label)
+		}
+		return pDim.Render(key+" ") + pBody.Render(label)
+	}
+
+	var left string
+	if m.size == small {
+		left = brand
+	} else {
+		left = strings.Join([]string{
+			brand,
+			tab("s", "shop", m.currentPage == shopPage),
+			tab("a", "account", m.currentPage == accountPage),
+		}, "   ")
+	}
+
+	cartLabel := pDim.Render("cart  ")
+	if m.inCartFlow() {
+		cartLabel = pWht.Bold(true).Render("cart  ")
+	}
+	cart := cartLabel +
+		lipgloss.NewStyle().Foreground(m.cartBlendColor()).Bold(true).
+			Render(fmt.Sprintf("$%d", m.CalculateSubtotal()/100)) +
+		pDim.Render(fmt.Sprintf("  ·  %d", m.CartItemCount()))
+
+	gap := wideW - lipgloss.Width(left) - lipgloss.Width(cart)
+	if gap < 1 {
+		gap = 1
+	}
+	row := left + strings.Repeat(" ", gap) + cart
+
+	return panel(wideW, 0, row)
 }

pkg/tui/help.go

@@ -1,8 +1,8 @@
 package tui
 
 import (
-	tea "github.com/charmbracelet/bubbletea"
-	"github.com/charmbracelet/lipgloss"
+	tea "charm.land/bubbletea/v2"
+	"charm.land/lipgloss/v2"
 )
 
 func (m Model) BuildHelpView() string {

pkg/tui/menu.go

@@ -1,9 +1,9 @@
 package tui
 
 import (
+	tea "charm.land/bubbletea/v2"
+	"charm.land/lipgloss/v2"
 	"fmt"
-	tea "github.com/charmbracelet/bubbletea"
-	"github.com/charmbracelet/lipgloss"
 )
 
 func (m Model) BuildMenuView() string {
@@ -32,12 +32,8 @@ func (m Model) BuildMenuView() string {
 
 	hint := base.Render("press esc to close")
 
-	itemCount := 0
-	total := 0
-	for _, item := range m.Cart {
-		total += item.Quantity * item.Coffee.Price
-		itemCount += item.Quantity
-	}
+	total := m.CalculateSubtotal()
+	itemCount := m.CartItemCount()
 
 	cartHint := base.Render(fmt.Sprintf("cart $%.2f [%d]", float64(total)/100, itemCount))