fix(webhook): fail closed when stripe webhook secret is not set

* fix: disable add-card-via-ssh, mark coming soo, skip in cursor nav

* style(tui): reword (coming soon) to (WIP)

.github/workflows/ci.yml

@@ -35,5 +35,31 @@ jobs:
         with:
           version: v2.4.0
 
+      - name: Install tparse
+        run: go install github.com/mfridman/tparse@v0.18.0
+
       - name: Test (race detector)
-        run: go test -race ./...
+        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

@@ -22,6 +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

@@ -33,6 +33,8 @@ api/api-server
 *.out
 coverage.txt
 coverage.html
+test-output.json
+test-report.xml
 
 # Dependency directories
 vendor/
@@ -114,3 +116,6 @@ ROADMAP.md
 
 *.bak
 terminalshop.prod.*
+
+# Backup verification config (real values; example file is committed)
+scripts/backups/config.env

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

@@ -71,3 +71,4 @@ 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

api/handlers/addresses.go

@@ -42,7 +42,7 @@ func (h *AddressHandler) GetAddresses(w http.ResponseWriter, r *http.Request) {
 	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,
 	})
 }
@@ -154,7 +154,7 @@ func (h *AddressHandler) CreateAddress(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusCreated, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusCreated, map[string]any{
 		"address": address,
 	})
 }
@@ -183,7 +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",
 	})
 }
@@ -218,7 +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

@@ -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 {

api/handlers/auth.go

@@ -108,7 +108,7 @@ func (h *AuthHandler) GetToken(w http.ResponseWriter, r *http.Request) {
 	}
 
 	middleware.RecordAuthAttempt("success")
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"access_token": token,
 		"token_type":   "Bearer",
 		"expires_in":   1800, // 30 minutes in seconds
@@ -146,7 +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
@@ -173,7 +173,7 @@ 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(),
 	})
 }
@@ -195,7 +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/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

@@ -5,8 +5,10 @@ import (
 	"encoding/hex"
 	"encoding/json"
 	"fmt"
+	"log/slog"
 	"net/http"
 	"strconv"
+	"strings"
 	"time"
 
 	"github.com/go-chi/chi/v5"
@@ -65,29 +67,34 @@ func PayRedirect(w http.ResponseWriter, r *http.Request) {
 
 // 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().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) {
@@ -107,7 +114,7 @@ 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,
 	})
 }
@@ -129,6 +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
@@ -140,7 +156,7 @@ 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,
 	})
 }
@@ -155,8 +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
@@ -181,7 +195,7 @@ func (h *CardHandler) CollectCard(w http.ResponseWriter, r *http.Request) {
 		utils.RespondError(w, http.StatusInternalServerError, "INTERNAL_ERROR", "failed to generate redirect token", nil)
 		return
 	}
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"url": fmt.Sprintf("%s/pay/%s", h.appURL, token),
 	})
 }
@@ -218,8 +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)
@@ -286,7 +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,
 	})
 }
@@ -319,7 +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{})
 	}
 
@@ -331,11 +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

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

@@ -5,8 +5,10 @@ import (
 	"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"
@@ -23,13 +25,20 @@ import (
 )
 
 type CartHandler struct {
-	stripeKey string
-	appURL    string
+	appURL        string
+	maxOrderCents int
 }
 
-// NewCartHandler creates a new cart handler with the Stripe secret key
-func NewCartHandler(stripeSecretKey, appURL string) *CartHandler {
-	return &CartHandler{stripeKey: stripeSecretKey, appURL: appURL}
+// 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.
@@ -46,18 +55,18 @@ func getOrCreateCart(ctx context.Context, userID uint) (*models.Cart, error) {
 	return &cart, nil
 }
 
-func cartResponse(ctx context.Context, cart *models.Cart) map[string]interface{} {
+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,
@@ -66,7 +75,7 @@ func cartResponse(ctx context.Context, cart *models.Cart) map[string]interface{}
 		})
 	}
 
-	return map[string]interface{}{
+	return map[string]any{
 		"items":            itemsData,
 		"subtotal":         subtotal,
 		"address_id":       cart.AddressID,
@@ -85,7 +94,7 @@ func (h *CartHandler) GetCart(w http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"cart": cartResponse(r.Context(), cart),
 	})
 }
@@ -148,7 +157,7 @@ func (h *CartHandler) SetItem(w http.ResponseWriter, r *http.Request) {
 		}
 	}
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"cart": cartResponse(r.Context(), cart),
 	})
 }
@@ -184,7 +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",
 	})
 }
@@ -209,6 +218,15 @@ func (h *CartHandler) SetCard(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
+	}
+
 	cart, err := getOrCreateCart(r.Context(), userID)
 	if err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "CART_ERROR", "failed to get cart", nil)
@@ -220,7 +238,7 @@ 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",
 	})
 }
@@ -240,7 +258,7 @@ 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",
 	})
 }
@@ -295,6 +313,16 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 		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")
@@ -302,8 +330,6 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 		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")
@@ -354,6 +380,18 @@ 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)
@@ -468,7 +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
@@ -495,14 +533,15 @@ func (h *CartHandler) ConvertCart(w http.ResponseWriter, r *http.Request) {
 	}
 	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 stays pending. the webhook flips it to paid once the customer
-// completes the bank-hosted challenge, the tui polls /api/v1/orders/{id}/status
+// 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()
 
@@ -529,13 +568,15 @@ func (h *CartHandler) respondRequiresAction(w http.ResponseWriter, order *models
 		return
 	}
 
-	// Persist the paymentIntent id AND reset status to pending. 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.
+	// 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.OrderStatusPending,
+		"status":            models.OrderStatusRequiresAction,
 	}).Error; err != nil {
 		utils.RespondError(w, http.StatusInternalServerError, "DATABASE_ERROR", "failed to save payment id", nil)
 		return
@@ -591,3 +632,149 @@ func appURLForHandler(r *http.Request) string {
 	}
 	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"
 )
@@ -65,7 +70,7 @@ func TestGetCartEmpty(t *testing.T) {
 	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"`
 	}
@@ -104,10 +109,10 @@ func TestSetItemAndGetCart(t *testing.T) {
 	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,
 	})
@@ -160,16 +165,16 @@ func TestSetItemUpdateQuantity(t *testing.T) {
 	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)
@@ -205,16 +210,16 @@ func TestSetItemRemove(t *testing.T) {
 	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)
@@ -228,7 +233,7 @@ 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"`
 	}
@@ -244,9 +249,9 @@ func TestSetItemInvalidProduct(t *testing.T) {
 	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)
@@ -261,9 +266,9 @@ func TestSetItemMissingCoffeeID(t *testing.T) {
 	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)
@@ -278,11 +283,11 @@ func TestClearCart(t *testing.T) {
 	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)
@@ -306,7 +311,7 @@ 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"`
 	}
@@ -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)
@@ -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)
@@ -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)
@@ -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)
@@ -485,10 +490,10 @@ func TestConvertCartMissingAddress(t *testing.T) {
 	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)
@@ -508,18 +513,18 @@ func TestConvertCartMissingCard(t *testing.T) {
 	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)
@@ -539,7 +544,7 @@ func TestConvertCartEmpty(t *testing.T) {
 	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)
@@ -556,11 +561,11 @@ func TestMultipleItems(t *testing.T) {
 	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)
@@ -578,8 +583,8 @@ 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"`
 	}
@@ -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)
@@ -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/orders.go

@@ -28,7 +28,6 @@ import (
 )
 
 type OrderHandler struct {
-	stripeKey           string
 	bringAPIUID         string
 	bringAPIKey         string
 	bringCustomerNumber string
@@ -44,9 +43,10 @@ type refundRequestPayload struct {
 // repeated submissions from spamming the operator's Slack channel.
 const refundRequestCooldown = 15 * time.Minute
 
-func NewOrderHandler(stripeSecretKey, bringAPIUID, bringAPIKey, bringCustomerNumber string) *OrderHandler {
+// 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{
-		stripeKey:           stripeSecretKey,
 		bringAPIUID:         bringAPIUID,
 		bringAPIKey:         bringAPIKey,
 		bringCustomerNumber: bringCustomerNumber,
@@ -200,8 +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),
 	})
@@ -221,7 +219,7 @@ 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",
 	})
@@ -287,7 +285,7 @@ func (h *OrderHandler) UpdateTracking(w http.ResponseWriter, r *http.Request) {
 
 	audit.OrderShipped(order.UserID, order.ID, req.Carrier, req.TrackingNumber)
 
-	utils.RespondSuccess(w, http.StatusOK, map[string]interface{}{
+	utils.RespondSuccess(w, http.StatusOK, map[string]any{
 		"order_id":        order.ID,
 		"carrier":         req.Carrier,
 		"tracking_number": req.TrackingNumber,

api/handlers/orders_test.go

@@ -60,7 +60,7 @@ func contextWithRoute(ctx context.Context, routeCtx *chi.Context) context.Contex
 func TestCreateRefundRequestRequiresMessageForOther(t *testing.T) {
 	user := setupOrderTestDB(t)
 
-	handler := NewOrderHandler("", "", "", "")
+	handler := NewOrderHandler("", "", "")
 	body := []byte(`{"reason":"Other","message":"   "}`)
 	req := orderRequest("POST", "/api/v1/orders/1/refund-request", body, user.ID, "1")
 	w := httptest.NewRecorder()
@@ -100,7 +100,7 @@ func TestCreateRefundRequestRejectsInvalidOrderState(t *testing.T) {
 		t.Fatalf("failed to create order: %v", err)
 	}
 
-	handler := NewOrderHandler("", "", "", "")
+	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()
@@ -142,7 +142,7 @@ func TestCreateRefundRequestEnforcesCooldown(t *testing.T) {
 		t.Fatalf("failed to create order: %v", err)
 	}
 
-	handler := NewOrderHandler("", "", "", "")
+	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()

api/handlers/products.go

@@ -30,7 +30,7 @@ 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,
 	})
 }
@@ -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/reconcile.go

@@ -1,10 +1,13 @@
 package handlers
 
 import (
+	"context"
 	"fmt"
 	"log/slog"
 	"time"
 
+	"terminalShop/api/middleware"
+	"terminalShop/pkg/audit"
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/models"
 	"terminalShop/pkg/notify"
@@ -14,15 +17,19 @@ import (
 	"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)
@@ -36,9 +43,14 @@ func ReconcileOrders(stripeKey string) {
 	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),
 			},
 		}
 
@@ -49,7 +61,7 @@ func ReconcileOrders(stripeKey string) {
 				"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 {
@@ -62,7 +74,7 @@ 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
@@ -77,10 +89,146 @@ func ReconcileOrders(stripeKey string) {
 	}
 }
 
-// ReconcileUnshipped finds paid order orlder than 24h with no tracking
-// number and posts single Slack reminder. Pure read + notif
-func ReconcileUnshipped() {
-	db := database.GetDB()
+// 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)
+		}
+	}
+}
+
+// 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)

api/handlers/reconcile_test.go

@@ -0,0 +1,520 @@
+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
+}

api/handlers/view.go

@@ -2,6 +2,7 @@ package handlers
 
 import (
 	"net/http"
+	"time"
 
 	"terminalShop/api/middleware"
 	"terminalShop/pkg/database"
@@ -11,6 +12,7 @@ import (
 	"gorm.io/gorm"
 )
 
+// ViewHandler handles bulk TUI bootstrap data
 type ViewHandler struct{}
 
 func NewViewHandler() *ViewHandler {
@@ -37,7 +39,10 @@ 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)
+	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).
@@ -49,7 +54,7 @@ func (h *ViewHandler) GetViewInit(w http.ResponseWriter, r *http.Request) {
 		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,

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

@@ -7,6 +7,7 @@ import (
 	"io"
 	"log/slog"
 	"net/http"
+	"os"
 	"strings"
 	"time"
 
@@ -28,13 +29,13 @@ 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, stripeKey, shippoSecret string) *WebhookHandler {
-	return &WebhookHandler{webhookSecret: webhookSecret, stripeKey: stripeKey, shippoSecret: shippoSecret}
+// 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.
@@ -52,8 +53,17 @@ 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.
-		webhookLog().Warn("stripe webhook secret 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{
@@ -124,8 +134,22 @@ func (h *WebhookHandler) handlePaymentIntentSucceeded(ctx context.Context, 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 {
@@ -139,7 +163,7 @@ func (h *WebhookHandler) handlePaymentIntentSucceeded(ctx context.Context, 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
@@ -150,6 +174,12 @@ func (h *WebhookHandler) handlePaymentIntentSucceeded(ctx context.Context, event
 		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)
 	go notify.SlackOrderPaid(&order)
 	webhookLog().Info("order marked paid", "order_id", orderIDStr, "pi", pi.ID)
@@ -178,7 +208,7 @@ func (h *WebhookHandler) handlePaymentIntentFailed(ctx context.Context, event st
 	}
 
 	db := database.GetDB().WithContext(ctx)
-	if err := db.Model(&models.Order{}).Where("id = ? AND status = ?", orderIDStr, models.OrderStatusPending).
+	if err := db.Model(&models.Order{}).Where("id = ? AND status IN (?, ?)", orderIDStr, models.OrderStatusPending, models.OrderStatusRequiresAction).
 		Update("status", models.OrderStatusFailed).Error; err != nil {
 		webhookLog().Error("failed to mark order failed", "order_id", orderIDStr, "error", err)
 	}
@@ -206,8 +236,6 @@ func (h *WebhookHandler) handleCheckoutSessionCompleted(ctx context.Context, eve
 		return
 	}
 
-	stripe.Key = h.stripeKey
-
 	si, err := setupintent.Get(sess.SetupIntent.ID, nil)
 	if err != nil {
 		webhookLog().Error("failed to get setup intent", "setup_intent", sess.SetupIntent.ID, "error", err)
@@ -255,8 +283,14 @@ func (h *WebhookHandler) handleCheckoutSessionCompleted(ctx context.Context, eve
 				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.
-			if uerr := db.Model(&dup).Update("updated_at", time.Now()).Error; uerr != nil {
+			// 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)
@@ -272,6 +306,7 @@ func (h *WebhookHandler) handleCheckoutSessionCompleted(ctx context.Context, eve
 		ExpMonth:        int(pm.Card.ExpMonth),
 		ExpYear:         int(pm.Card.ExpYear),
 	}
+	card.InitializeStorageTTL(time.Now())
 
 	if err := db.Create(&card).Error; err != nil {
 		webhookLog().Error("failed to save card", "user_id", user.ID, "error", err)

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

@@ -19,6 +19,8 @@ import (
 	"terminalShop/pkg/database"
 	"terminalShop/pkg/observability"
 	"terminalShop/pkg/stripeclient"
+
+	"github.com/stripe/stripe-go/v78"
 )
 
 const version = "v0.1.0"
@@ -49,6 +51,12 @@ func main() {
 	}
 	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)
@@ -71,7 +79,7 @@ func main() {
 	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.BringCustomerNumber, cfg.ShippoWebhookSecret, cfg.AppURL, cfg.SlackSigningSecret, cfg.AdminAPIKey, cfg.APIPort)
+	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{
@@ -106,7 +114,7 @@ func main() {
 		for {
 			select {
 			case <-ticker.C:
-				handlers.ReconcileOrders(cfg.StripeSecretKey)
+				handlers.ReconcileOrders(ctx)
 			case <-ctx.Done():
 				return
 			}
@@ -114,14 +122,48 @@ func main() {
 	}()
 
 	go func() {
-		time.Sleep(30 * time.Second)
-		handlers.ReconcileUnshipped()
+		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()
+				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
 			}
@@ -136,10 +178,10 @@ 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/metrics.go

@@ -70,6 +70,14 @@ var (
 		[]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",
@@ -173,6 +181,19 @@ 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)

api/routes/routes.go

@@ -16,7 +16,6 @@ import (
 // SetupRoutes configures all API routes
 func SetupRoutes(
 	version string,
-	stripeSecretKey string,
 	stripeWebhookSecret string,
 	jwtManager *auth.JWTManager,
 	authFingerprintKey string,
@@ -29,6 +28,7 @@ func SetupRoutes(
 	slackSigningSecret string,
 	adminAPIKey string,
 	apiPort string,
+	maxOrderCents int,
 ) *chi.Mux {
 	r := chi.NewRouter()
 
@@ -46,12 +46,12 @@ func SetupRoutes(
 	healthHandler := handlers.NewHealthHandler(version)
 	productHandler := handlers.NewProductHandler()
 	authHandler := handlers.NewAuthHandler(jwtManager, authFingerprintKey)
-	cartHandler := handlers.NewCartHandler(stripeSecretKey, appURL)
-	cardHandler := handlers.NewCardHandler(stripeSecretKey, appURL)
-	orderHandler := handlers.NewOrderHandler(stripeSecretKey, bringAPIUID, bringAPIKey, bringCustomerNumber)
+	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, shippoWebhookSecret)
+	webhookHandler := handlers.NewWebhookHandler(stripeWebhookSecret, shippoWebhookSecret)
 	slackHandler := handlers.NewSlackHandler(slackSigningSecret, adminAPIKey, apiPort, shippoWebhookSecret)
 
 	// Short payment redirect and success page — no auth required.
@@ -131,6 +131,7 @@ 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)
 

go.mod

@@ -39,6 +39,7 @@ require (
 	github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be // indirect
 	github.com/atotto/clipboard v0.1.4 // 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/cenkalti/backoff/v5 v5.0.3 // indirect
 	github.com/cespare/xxhash/v2 v2.3.0 // indirect
@@ -56,15 +57,20 @@ require (
 	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/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
@@ -75,7 +81,10 @@ require (
 	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/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-runewidth v0.0.23 // indirect
 	github.com/mattn/go-sqlite3 v1.14.34 // indirect
 	github.com/mitchellh/hashstructure/v2 v2.0.2 // indirect
@@ -98,10 +107,13 @@ require (
 	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
@@ -109,4 +121,10 @@ require (
 	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

@@ -26,6 +26,8 @@ github.com/aymanbagabas/go-udiff v0.4.1 h1:OEIrQ8maEeDBXQDoGCbbTTXYJMYRCRO1fnodZ
 github.com/aymanbagabas/go-udiff v0.4.1/go.mod h1:0L9PGwj20lrtmEMeyw4WKJ/TMyDtvAoK9bf2u/mNo3w=
 github.com/beorn7/perks v1.0.1 h1:VlbKKnNfV8bJzeqoa4cOKqO6bYr3WgKZxO8Z16+hsOM=
 github.com/beorn7/perks v1.0.1/go.mod h1:G2ZrVWU2WbWT9wwq4/hrbKbnv/1ERSJQ0ibhJ6rlkpw=
+github.com/bitfield/gotestdox v0.2.2 h1:x6RcPAbBbErKLnapz1QeAlf3ospg8efBsedU93CDsnE=
+github.com/bitfield/gotestdox v0.2.2/go.mod h1:D+gwtS0urjBrzguAkTM2wodsTQYFHdpx8eqRJ3N+9pY=
 github.com/catppuccin/go v0.3.0 h1:d+0/YicIq+hSTo5oPuRi5kOpqkVA5tAsU6dNhvRu+aY=
 github.com/catppuccin/go v0.3.0/go.mod h1:8IHJuMGaUUjQM82qBrGNBv7LFq6JI3NnQCF6MOlZjpc=
 github.com/cenkalti/backoff/v5 v5.0.3 h1:ZN+IMa753KfX5hd8vVaMixjnqRZ3y8CuJKRKj1xcsSM=
@@ -69,12 +71,18 @@ github.com/creack/pty v1.1.24/go.mod h1:08sCNb52WyoAwi2QDyzUCTgcvVFhUzewun7wtTfv
 github.com/davecgh/go-spew v1.1.0/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
 github.com/davecgh/go-spew v1.1.1 h1:vj9j/u1bqnvCEfJOwUhtlOARqs3+rkHYY13jYWTU97c=
 github.com/davecgh/go-spew v1.1.1/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
+github.com/dnephin/pflag v1.0.7 h1:oxONGlWxhmUct0YzKTgrpQv9AUA1wtPBn7zuSjJqptk=
+github.com/dnephin/pflag v1.0.7/go.mod h1:uxE91IoWURlOiTUIA8Mq5ZZkAv3dPUfZNaT80Zm7OQE=
 github.com/dustin/go-humanize v1.0.1 h1:GzkhY7T5VNhEkwH0PVJgjz+fX1rhBrR7pRT3mDkpeCY=
 github.com/dustin/go-humanize v1.0.1/go.mod h1:Mu1zIs6XwVuF/gI1OepvI0qD18qycQx+mFykh5fBlto=
+github.com/fatih/color v1.18.0 h1:S8gINlzdQ840/4pfAwic/ZE0djQEH3wM94VfqLTZcOM=
+github.com/fatih/color v1.18.0/go.mod h1:4FelSpRwEGDpQ12mAdzqdOukCy4u8WUtOY6lkT/6HfU=
 github.com/felixge/httpsnoop v1.0.4 h1:NFTV2Zj1bL4mc9sqWACXbQFVBBg2W3GPvqp8/ESS2Wg=
 github.com/felixge/httpsnoop v1.0.4/go.mod h1:m8KPJKqk1gH5J9DgRY2ASl2lWCfGKXixSwevea8zH2U=
 github.com/foize/go.sgr v0.0.0-20140220094842-40bdfc98040c h1:NhHTf8Ewd3NS46DylZB75Zi0UeATvDbDwFEmsO5ZVpQ=
 github.com/foize/go.sgr v0.0.0-20140220094842-40bdfc98040c/go.mod h1:0ghtL4RhKBjyWMkHCWosp2aHSEXShQeQMLQ0qBCytfU=
+github.com/fsnotify/fsnotify v1.9.0 h1:2Ml+OJNzbYCTzsxtv8vKSFD9PbJjmhYF14k/jKC7S9k=
+github.com/fsnotify/fsnotify v1.9.0/go.mod h1:8jBTzvmWwFyi3Pb8djgCCO5IBqzKJ/Jwo8TRcHyHii0=
 github.com/go-chi/chi/v5 v5.2.5 h1:Eg4myHZBjyvJmAFjFvWgrqDTXFyOzjj7YIm3L3mu6Ug=
 github.com/go-chi/chi/v5 v5.2.5/go.mod h1:X7Gx4mteadT3eDOMTsXzmI4/rwUpOwBHLpAfupzFJP0=
 github.com/go-chi/cors v1.2.2 h1:Jmey33TE+b+rB7fT8MUy1u0I4L+NARQlK6LhzKPSyQE=
@@ -105,8 +113,12 @@ github.com/google/go-cmp v0.5.2/go.mod h1:v8dTdLbMG2kIc/vJvl+f65V22dbkXbowE6jgT/
 github.com/google/go-cmp v0.5.5/go.mod h1:v8dTdLbMG2kIc/vJvl+f65V22dbkXbowE6jgT/gNBxE=
 github.com/google/go-cmp v0.7.0 h1:wk8382ETsv4JYUZwIsn6YpYiWiBsYLSJiTsyBybVuN8=
 github.com/google/go-cmp v0.7.0/go.mod h1:pXiqmnSA92OHEEa9HXL2W4E7lf9JzCmGVUdgjX3N/iU=
+github.com/google/shlex v0.0.0-20191202100458-e7afc7fbc510 h1:El6M4kTTCOh6aBiKaUGG7oYTSPP8MxqL4YI3kZKwcP4=
+github.com/google/shlex v0.0.0-20191202100458-e7afc7fbc510/go.mod h1:pupxD2MaaD3pAXIBCelhxNneeOaAeabZDe5s4K6zSpQ=
 github.com/google/uuid v1.6.0 h1:NIvaJDMOsjHA8n1jAhLSgzrAzy1Hgr+hNrb57e+94F0=
 github.com/google/uuid v1.6.0/go.mod h1:TIyPZe4MgqvfeYDBFedMoGGpEw/LqOeaOT+nhxU+yHo=
+github.com/gotesttools/gotestfmt/v2 v2.5.0 h1:fSU3MnR+E+fvuXdw1l8xbufKhDxY3Tfjsjx/I1WerB4=
+github.com/gotesttools/gotestfmt/v2 v2.5.0/go.mod h1:oQJg2KZ2aGoqEbMC2PDaAeBYm0tOkocgixK9FzsCdp4=
 github.com/grpc-ecosystem/grpc-gateway/v2 v2.28.0 h1:HWRh5R2+9EifMyIHV7ZV+MIZqgz+PMpZ14Jynv3O2Zs=
 github.com/grpc-ecosystem/grpc-gateway/v2 v2.28.0/go.mod h1:JfhWUomR1baixubs02l85lZYYOm7LV6om4ceouMv45c=
 github.com/hashicorp/go-version v1.6.0 h1:feTTfFNnjP967rlCxM/I9g701jU+RN74YKx2mOkIeek=
@@ -143,6 +155,11 @@ github.com/kylelemons/godebug v1.1.0 h1:RPNrshWIDI6G2gRW9EHilWtl7Z6Sb1BR0xunSBf0
 github.com/kylelemons/godebug v1.1.0/go.mod h1:9/0rRGxNHcop5bhtWyNeEfOS8JIWk580+fNqagV/RAw=
 github.com/lucasb-eyer/go-colorful v1.4.0 h1:UtrWVfLdarDgc44HcS7pYloGHJUjHV/4FwW4TvVgFr4=
 github.com/lucasb-eyer/go-colorful v1.4.0/go.mod h1:R4dSotOR9KMtayYi1e77YzuveK+i7ruzyGqttikkLy0=
+github.com/mattn/go-colorable v0.1.13 h1:fFA4WZxdEF4tXPZVKMLwD8oUnCTTo08duU7wxecdEvA=
+github.com/mattn/go-colorable v0.1.13/go.mod h1:7S9/ev0klgBDR4GtXTXX8a3vIGJpMovkB8vQcUbaXHg=
+github.com/mattn/go-isatty v0.0.16/go.mod h1:kYGgaQfpe5nmfYZH+SKPsOc2e4SrIfOl2e/yFXSvRLM=
+github.com/mattn/go-isatty v0.0.20 h1:xfD0iDuEKnDkl03q4limB+vH+GxLEtL/jb4xVJSWWEY=
+github.com/mattn/go-isatty v0.0.20/go.mod h1:W+V8PltTTMOvKvAeJH7IuucS94S2C6jfK/D7dTCTo3Y=
 github.com/mattn/go-runewidth v0.0.23 h1:7ykA0T0jkPpzSvMS5i9uoNn2Xy3R383f9HDx3RybWcw=
 github.com/mattn/go-runewidth v0.0.23/go.mod h1:XBkDxAl56ILZc9knddidhrOlY5R/pDhgLpndooCuJAs=
 github.com/mattn/go-sqlite3 v1.14.34 h1:3NtcvcUnFBPsuRcno8pUtupspG/GM+9nZ88zgJcp6Zk=
@@ -239,6 +256,8 @@ golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546 h1:mgKeJMpvi0yx/sU5GsxQ7p6s2
 golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546/go.mod h1:j/pmGrbnkbPtQfxEe5D0VQhZC6qKbfKifgD0oM7sR70=
 golang.org/x/mod v0.2.0/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
 golang.org/x/mod v0.3.0/go.mod h1:s0Qsj1ACt9ePp/hMypM3fl4fZqREWJwdYDEqhRiZZUA=
+golang.org/x/mod v0.34.0 h1:xIHgNUUnW6sYkcM5Jleh05DvLOtwc6RitGHbDk4akRI=
+golang.org/x/mod v0.34.0/go.mod h1:ykgH52iCZe79kzLLMhyCUzhMci+nQj+0XkbXpNYtVjY=
 golang.org/x/net v0.0.0-20190404232315-eb5bcb51f2a3/go.mod h1:t9HGtf8HONx5eT2rtn7q6eTqICYqUVnKs3thJo3Qplg=
 golang.org/x/net v0.0.0-20190620200207-3b0461eec859/go.mod h1:z5CRVTTTmAJ677TzLLGU+0bjPO0LkuOLi4/5GtJWs/s=
 golang.org/x/net v0.0.0-20200226121028-0de0cce0169b/go.mod h1:z5CRVTTTmAJ677TzLLGU+0bjPO0LkuOLi4/5GtJWs/s=
@@ -259,6 +278,8 @@ golang.org/x/sys v0.0.0-20200930185726-fdedc70b468f/go.mod h1:h1NjWce9XRLGQEsW7w
 golang.org/x/sys v0.0.0-20201119102817-f84b799fce68/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20210423082822-04245dca01da/go.mod h1:h1NjWce9XRLGQEsW7wpKNCjG9DtNlClVuFLEZdDNbEs=
 golang.org/x/sys v0.0.0-20210615035016-665e8c7367d1/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
+golang.org/x/sys v0.0.0-20220811171246-fbc7d0a398ab/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
+golang.org/x/sys v0.6.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.43.0 h1:Rlag2XtaFTxp19wS8MXlJwTvoh8ArU6ezoyFsMyCTNI=
 golang.org/x/sys v0.43.0/go.mod h1:4GL1E5IUh+htKOUEOaiffhrAeqysfVGipDYzABqnCmw=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
@@ -274,6 +295,8 @@ golang.org/x/tools v0.0.0-20180917221912-90fa682c2a6e/go.mod h1:n7NCudcB/nEzxVGm
 golang.org/x/tools v0.0.0-20191119224855-298f0cb1881e/go.mod h1:b+2E5dAYhXwXZwtnZ6UAqBI28+e2cm9otk0dWdXHAEo=
 golang.org/x/tools v0.0.0-20200619180055-7c47624df98f/go.mod h1:EkVYQZoAsY45+roYkvgYkIh4xh/qjgUK9TdY2XT94GE=
 golang.org/x/tools v0.0.0-20210106214847-113979e3529a/go.mod h1:emZCQorbCU4vsT4fOWvOPXz4eW1wZW4PmDk9uLelYpA=
+golang.org/x/tools v0.43.0 h1:12BdW9CeB3Z+J/I/wj34VMl8X+fEXBxVR90JeMX5E7s=
+golang.org/x/tools v0.43.0/go.mod h1:uHkMso649BX2cZK6+RpuIPXS3ho2hZo4FVwfoy1vIk0=
 golang.org/x/xerrors v0.0.0-20190717185122-a985d3407aa7/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 golang.org/x/xerrors v0.0.0-20191011141410-1b5146add898/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 golang.org/x/xerrors v0.0.0-20191204190536-9bdfabe68543/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
@@ -310,5 +333,9 @@ gorm.io/gorm v1.31.1 h1:7CA8FTFz/gRfgqgpeKIBcervUn3xSyPUmr6B2WXJ7kg=
 gorm.io/gorm v1.31.1/go.mod h1:XyQVbO2k6YkOis7C2437jSit3SsDK72s7n7rsSHd+Gs=
 gorm.io/plugin/opentelemetry v0.1.16 h1:Kypj2YYAliJqkIczDZDde6P6sFMhKSlG5IpngMFQGpc=
 gorm.io/plugin/opentelemetry v0.1.16/go.mod h1:P3RmTeZXT+9n0F1ccUqR5uuTvEXDxF8k2UpO7mTIB2Y=
+gotest.tools/gotestsum v1.13.0 h1:+Lh454O9mu9AMG1APV4o0y7oDYKyik/3kBOiCqiEpRo=
+gotest.tools/gotestsum v1.13.0/go.mod h1:7f0NS5hFb0dWr4NtcsAsF0y1kzjEFfAil0HiBQJE03Q=
+gotest.tools/v3 v3.5.2 h1:7koQfIKdy+I8UTetycgUqXWSDwpgv193Ka+qRsmBY8Q=
+gotest.tools/v3 v3.5.2/go.mod h1:LtdLGcnqToBH83WByAAi/wiwSFCArdFIUV/xxN4pcjA=
 rsc.io/qr v0.2.0 h1:6vBLea5/NRMVTz8V66gipeLycZMl/+UlFmk8DvqQ6WY=
 rsc.io/qr v0.2.0/go.mod h1:IF+uZjkb9fqyeF/4tlBoynqmQxUoPfWEKh921coOuXs=

main.go

@@ -8,7 +8,6 @@ import (
 	"os"
 	"os/signal"
 	"syscall"
-
 	"time"
 
 	tea "charm.land/bubbletea/v2"
@@ -16,6 +15,7 @@ import (
 	"charm.land/wish/v2/bubbletea"
 	"charm.land/wish/v2/logging"
 	"github.com/charmbracelet/ssh"
+	"github.com/stripe/stripe-go/v78"
 
 	"terminalShop/pkg/auth"
 	"terminalShop/pkg/config"
@@ -32,7 +32,6 @@ func listenHost() string {
 var (
 	apiURL             string
 	authFingerprintKey string
-	stripePublicKey    string
 )
 
 func teaHandler(s ssh.Session) (tea.Model, []tea.ProgramOption) {
@@ -44,7 +43,7 @@ func teaHandler(s ssh.Session) (tea.Model, []tea.ProgramOption) {
 		pubKeyStr = auth.FormatSSHPublicKey(pubKey)
 	}
 
-	m := tui.NewModelWithAuth(fingerprint, pubKeyStr, apiURL, authFingerprintKey, stripePublicKey)
+	m := tui.NewModelWithAuth(fingerprint, pubKeyStr, apiURL, authFingerprintKey)
 	return m, nil
 }
 
@@ -58,7 +57,15 @@ 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

pkg/api/client.go

@@ -104,16 +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
@@ -339,7 +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,
 	}
@@ -379,7 +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)
@@ -418,7 +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)
@@ -563,6 +563,58 @@ func (c *Client) GetOrderStatus(id uint) (string, error) {
 	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.
 func (c *Client) GetCards() ([]models.Card, error) {
 	url := fmt.Sprintf("%s/api/v1/cards", c.BaseURL)

pkg/audit/audit.go

@@ -13,16 +13,36 @@ import (
 	"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"
+	eventCardExpired            eventType = "card_expired"
 	eventOrderCreated           eventType = "order_created"
 	eventOrderPaid              eventType = "order_paid"
 	eventOrderShipped           eventType = "order_shipped"
 	eventOrderFailed            eventType = "order_failed"
-	eventOrderRequiresAction    eventType = "order_requires_action"
+	eventOrderRequiresAction    eventType = EventOrderRequiresAction
+	eventOrder3DSAbandoned      eventType = EventOrder3DSAbandoned
+	eventCartRejected           eventType = EventCartRejected
 	eventOrderRefunded          eventType = "order_refunded"
 	eventPaymentCritical        eventType = "payment_critical"
 	eventLabelPurchased         eventType = "label_purchased"
@@ -33,19 +53,21 @@ const (
 )
 
 type event struct {
-	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
+	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 (e event) attrs() []any {
@@ -86,6 +108,12 @@ func (e event) attrs() []any {
 	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
 }
 
@@ -113,6 +141,17 @@ func CardDeleted(userID, cardID uint) {
 	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) {
 	e := event{
@@ -301,7 +340,6 @@ func attrsToMap(a []any) map[string]any {
 	return m
 }
 
-//nolint:unused // called from ConvertCart in the next update
 func OrderRequiresAction(userID, orderID uint, paymentIntentID string) {
 	e := event{
 		Event:    eventOrderRequiresAction,
@@ -312,3 +350,33 @@ func OrderRequiresAction(userID, orderID uint, paymentIntentID string) {
 	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/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/config/config.go

@@ -3,8 +3,10 @@ package config
 import (
 	"errors"
 	"fmt"
+	"log/slog"
 	"net/url"
 	"os"
+	"strconv"
 	"strings"
 
 	"github.com/joho/godotenv"
@@ -12,24 +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
-	BringCustomerNumber string
-	ShippoWebhookSecret string
-	SlackSigningSecret  string
-	AdminAPIKey         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.
@@ -48,24 +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"),
-		BringCustomerNumber: os.Getenv("BRING_CUSTOMER_NUMBER"),
-		ShippoWebhookSecret: os.Getenv("SHIPPO_WEBHOOK_SECRET"),
-		SlackSigningSecret:  os.Getenv("SLACK_SIGNING_SECRET"),
-		AdminAPIKey:         os.Getenv("ADMIN_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 {
@@ -86,6 +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
@@ -130,3 +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/database/migrate.go

@@ -3,6 +3,7 @@ package database
 import (
 	"fmt"
 	"log"
+	"time"
 
 	"terminalShop/pkg/models"
 
@@ -30,6 +31,18 @@ func Migrate(db *gorm.DB) error {
 		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
@@ -27,7 +28,7 @@ func Seed(db *gorm.DB) error {
 			RoastType:   "Dark Roast",
 			Ounces:      2,
 			BeanType:    "Arabica",
-			Price:       350, // $3.50
+			Price:       1800, // $18.00
 			Color:       "#8B4513",
 			Description: "Bold and intense coffee with a rich crema",
 		},
@@ -36,7 +37,7 @@ func Seed(db *gorm.DB) error {
 			RoastType:   "Medium Roast",
 			Ounces:      8,
 			BeanType:    "Arabica",
-			Price:       400, // $4.00
+			Price:       2200, // $22.00
 			Color:       "#A0522D",
 			Description: "Smooth and balanced espresso diluted with hot water",
 		},
@@ -45,7 +46,7 @@ func Seed(db *gorm.DB) error {
 			RoastType:   "Medium Roast",
 			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",
 		},
@@ -54,7 +55,7 @@ func Seed(db *gorm.DB) error {
 			RoastType:   "Medium Roast",
 			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",
 		},
@@ -63,7 +64,7 @@ func Seed(db *gorm.DB) error {
 			RoastType:   "Dark Roast",
 			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.",
 		},
@@ -72,7 +73,7 @@ func Seed(db *gorm.DB) error {
 			RoastType:   "Dark Roast",
 			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/order.go

@@ -10,13 +10,14 @@ 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

pkg/models/order_display.go

@@ -35,6 +35,8 @@ func (order *Order) DisplayState() string {
 	switch order.Status {
 	case OrderStatusPending:
 		return "Awaiting payment"
+	case OrderStatusRequiresAction:
+		return "Awaiting authentication"
 	case OrderStatusPaid:
 		if order.TrackingNumber == "" {
 			return "Paid * awaiting label"
@@ -77,6 +79,8 @@ func (order *Order) DisplayKind() DisplayKind {
 	switch order.Status {
 	case OrderStatusPending:
 		return DisplayKindNeutral
+	case OrderStatusRequiresAction:
+		return DisplayKindNeutral
 	case OrderStatusPaid:
 		return DisplayKindAccent
 	case OrderStatusShipped:

pkg/models/order_display_test.go

@@ -14,6 +14,7 @@ func TestOrderDisplayState(t *testing.T) {
 		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},

pkg/tui/confirmation.go

@@ -170,8 +170,20 @@ 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 esc to try again")
+		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),
@@ -208,7 +220,7 @@ func (m Model) renderRequiresActionView() string {
 	header := m.theme.TextAccent().Bold(true).Render("your bank wants to verify this charge")
 
 	if m.review.redirectURL == "" {
-		return base.Render("  waiting for authentication link...")
+		return base.Render("  verifying with your bank...")
 	}
 
 	qr, qrSize, err := qrfefe.Generate(m.review.redirectURL)
@@ -233,12 +245,11 @@ func (m Model) ReviewUpdate(msg tea.Msg) (Model, tea.Cmd) {
 	case CheckoutResultMsg:
 		m.CheckingOut = false
 		if msg.Err != nil {
-			m = m.SwitchPage(paymentPage)
+			var cmd tea.Cmd
+			m, cmd = m.switchForCheckoutError(msg.Err)
 			m.error = &VisibleError{message: friendlyCheckoutError(msg.Err)}
 			m.review.cardJustAdded = false
-			m.payment.view = 0
-			m.payment.form = nil
-			return m, nil
+			return m, cmd
 		}
 		if msg.RequiresAction {
 			m.review.requiresAction = true
@@ -275,17 +286,65 @@ func (m Model) ReviewUpdate(msg tea.Msg) (Model, tea.Cmd) {
 			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 {
-			if msg.String() == "esc" || msg.String() == "enter" {
+			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
@@ -294,6 +353,17 @@ func (m Model) ReviewUpdate(msg tea.Msg) (Model, tea.Cmd) {
 			}
 			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
@@ -330,13 +400,29 @@ 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"):

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/model.go

@@ -75,7 +75,6 @@ type Model struct {
 	Fingerprint        string
 	AccessToken        string
 	AuthFingerprintKey string // shared secret for /auth/token refresh
-	StripePublicKey    string
 
 	// One-shop auth command - capture pubKeyStr in closure, not stored on Model
 	authCmd tea.Cmd
@@ -211,6 +210,8 @@ type reviewState struct {
 	redirectURL    string
 	orderID        uint
 	authFailed     bool
+	retrying       bool
+	retryExhausted bool
 }
 
 type confirmState struct {
@@ -442,6 +443,18 @@ type OrderStatusMsg struct {
 	Err     error
 }
 
+// RetryAuthResultMsg carries the outcome of POST /orders/{id}/retry-auth.
+// Status "requires_action" -> RedirectURL is a fresh challenge URL; resume
+// the QR + poll loop. Status "succeeded" -> frictionless retry approved;
+// server's APIError string ("RETRY_LIMIT" / "CARD_NO_LONGER_AVAILABLE" /
+// transient) - the Update branch matches on substring.
+type RetryAuthResultMsg struct {
+	OrderID     uint
+	Status      string
+	RedirectURL string
+	Err         error
+}
+
 // CartSyncedMsg is recieved when the server responds to a cart item update
 type CartSyncedMsg struct {
 	UpdateID int64
@@ -682,6 +695,23 @@ func (m Model) schedulePollOrderStatus(orderID uint) tea.Cmd {
 	})
 }
 
+func (m Model) retryAuthCmd(orderID uint) tea.Cmd {
+	return func() tea.Msg {
+		if m.APIClient == nil {
+			return RetryAuthResultMsg{OrderID: orderID, Err: fmt.Errorf("api client unavailable")}
+		}
+		outcome, err := m.APIClient.RetryAuth(orderID)
+		if err != nil {
+			return RetryAuthResultMsg{OrderID: orderID, Err: err}
+		}
+		return RetryAuthResultMsg{
+			OrderID:     orderID,
+			Status:      outcome.Status,
+			RedirectURL: outcome.RedirectURL,
+		}
+	}
+}
+
 func (m Model) syncCartItemCmd(coffeeID uint, quantity int) (Model, tea.Cmd) {
 	if m.APIClient == nil || m.User == nil {
 		return m, nil
@@ -705,7 +735,6 @@ func (m Model) saveCardOnlyCmd(form PaymentFormCompleteMsg) tea.Cmd {
 		if m.APIClient == nil {
 			return CardSavedForReviewMsg{Err: fmt.Errorf("API client not available")}
 		}
-		stripe.Key = m.StripePublicKey
 		tok, err := stripetoken.New(&stripe.TokenParams{
 			Card: &stripe.CardParams{
 				Name:       stripe.String(form.CardName),
@@ -874,11 +903,12 @@ func NewModel(username string) Model {
 }
 
 // NewModelWithAuth creates a new model with user authentication context.
-func NewModelWithAuth(fingerprint string, pubKeyStr string, apiURL string, clientSecret string, stripePublicKey string) Model {
+// The publishable Stripe key is wired into stripe.Key once at startup in
+// the SSH binary's main, so it is not threaded through here.
+func NewModelWithAuth(fingerprint string, pubKeyStr string, apiURL string, clientSecret string) Model {
 	m := NewModel("")
 	m.Fingerprint = fingerprint
 	m.AuthFingerprintKey = clientSecret
-	m.StripePublicKey = stripePublicKey
 	m.currentPage = splashPage
 	if apiURL != "" {
 		m.APIClient = api.NewClient(apiURL, "")

pkg/tui/payment_form.go

@@ -355,11 +355,16 @@ func (m Model) RenderCardList() string {
 		boxes = append(boxes, box)
 	}
 
-	sshFocused := m.payment.cardCursor == len(m.SavedCards)
-	sshBox := m.CreateBox(m.formatListItem("+ add card via ssh", sshFocused), sshFocused)
+	// SSH inline card-add is dormant until i have a norwegian org
+	// number wired to stripe, something i dont have since its $300+. Keep the row visible so the option is
+	// discoverable, but render it dimmed and exclude it from cursor space
+	// (handled in PaymentUpdate below) so it can not be picked
+	dim := m.theme.TextDim().Render
+	sshLabel := dim("+ add card via ssh") + "  " + dim("(WIP)")
+	sshBox := m.CreateBox(m.formatListItem(sshLabel, false), false)
 	boxes = append(boxes, sshBox)
 
-	httpsFocused := m.payment.cardCursor == len(m.SavedCards)+1
+	httpsFocused := m.payment.cardCursor == len(m.SavedCards)
 	httpsBox := m.CreateBox(m.formatListItem("+ add payment via browser", httpsFocused), httpsFocused)
 	boxes = append(boxes, httpsBox)
 
@@ -501,7 +506,7 @@ func (m Model) PaymentUpdate(msg tea.Msg) (Model, tea.Cmd) {
 				m.payment.cardCursor--
 			}
 		case "down", "j":
-			if m.payment.cardCursor < len(m.SavedCards)+1 {
+			if m.payment.cardCursor < len(m.SavedCards) {
 				m.payment.cardCursor++
 			}
 
@@ -511,17 +516,8 @@ func (m Model) PaymentUpdate(msg tea.Msg) (Model, tea.Cmd) {
 				m.SelectedCard = &selected
 				return m.ReviewSwitch()
 			}
-			if m.payment.cardCursor == len(m.SavedCards) {
-				m.payment.view = 1
-				m.payment.form = m.InitPaymentForm()
-				m.footer = []footerCommand{
-					{key: "tab", value: "next"},
-					{key: "enter", value: "submit"},
-					{key: "esc", value: "back"},
-				}
-				return m, m.payment.form.form.Init()
-			}
-			// Browser payment
+			// Browser flow, the only reachable add-card path while the SSH
+			// inline form is dormant (see RenderCardList)
 			m.payment.view = 2
 			m.payment.collectURL = nil
 			m.payment.collectTimeOut = false
@@ -546,16 +542,6 @@ func (m Model) PaymentUpdate(msg tea.Msg) (Model, tea.Cmd) {
 				if m.payment.cardCursor >= len(m.SavedCards) && m.payment.cardCursor > 0 {
 					m.payment.cardCursor--
 				}
-				if len(m.SavedCards) == 0 {
-					m.payment.view = 1
-					m.payment.form = m.InitPaymentForm()
-					m.footer = []footerCommand{
-						{key: "tab", value: "next"},
-						{key: "enter", value: "submit"},
-						{key: "esc", value: "back"},
-					}
-					return m, tea.Batch(m.payment.form.form.Init(), m.deleteCardCmd(card.ID))
-				}
 				return m, m.deleteCardCmd(card.ID)
 			}
 		}

pkg/tui/payment_form_test.go

@@ -0,0 +1,91 @@
+package tui
+
+import (
+	"strings"
+	"testing"
+
+	"terminalShop/pkg/models"
+
+	tea "charm.land/bubbletea/v2"
+)
+
+// newPaymentCardListModel parks a Model on the payment page card-list view
+// with n synthetic saved cards. Baseline for assertint that the dormant
+// "+ add card via ssh" row is dimmed and unreachable by cursor navigation.
+func newPaymentCardListModel(t *testing.T, n int) Model {
+	t.Helper()
+	m := NewModel("test")
+	m = m.updateLayout(120, 40)
+	m.currentPage = paymentPage
+	m.payment.view = 0
+	m.payment.form = nil
+	m.payment.cardCursor = 0
+	for i := range n {
+		m.SavedCards = append(m.SavedCards, models.Card{
+			ID:       uint(i + 1),
+			Brand:    "visa",
+			Last4:    "4242",
+			ExpMonth: 12,
+			ExpYear:  2030,
+		})
+	}
+	return m
+}
+
+func keyEnter() tea.KeyMsg { return tea.KeyPressMsg{Code: tea.KeyEnter} }
+
+func TestRenderCardList_SshOptionComingSoon(t *testing.T) {
+	m := newPaymentCardListModel(t, 1)
+	out := m.RenderCardList()
+	if !strings.Contains(out, "add card via ssh") {
+		t.Fatalf("ssh option missing from card list output:\n%s", out)
+	}
+	if !strings.Contains(out, "WIP") {
+		t.Fatalf("want 'WIP' marked on ssh option:\n%s", out)
+	}
+}
+
+func TestPaymentUpdate_DownNavigationStopsAtBrowserSlot(t *testing.T) {
+	m := newPaymentCardListModel(t, 2)
+	for range 10 {
+		var cmd tea.Cmd
+		m, cmd = m.PaymentUpdate(keyJ())
+		_ = cmd
+	}
+	want := len(m.SavedCards) // browser slot; ssh slot in unreachable
+	if m.payment.cardCursor != want {
+		t.Fatalf("cursor stopped at %d, want %d (browser slot)", m.payment.cardCursor, want)
+	}
+}
+
+func TestPaymentUpdate_EnterOnBrowserSlotLaunchesBrowserFlow(t *testing.T) {
+	m := newPaymentCardListModel(t, 1)
+	m.payment.cardCursor = len(m.SavedCards) // browser slot
+	newM, cmd := m.PaymentUpdate(keyEnter())
+	if newM.payment.view != 2 {
+		t.Fatalf("payment.view = %d, want 2 (browser flow)", newM.payment.view)
+	}
+	if newM.payment.form != nil {
+		t.Fatalf("payment.form must be nil after enter; ssh inline form is dormant")
+	}
+	if cmd == nil {
+		t.Fatalf("expected collectCardCmd, got nil")
+	}
+}
+
+func TestPaymentUpdate_EnterWithZeroCardsLaunchesBrowserFlow(t *testing.T) {
+	m := newPaymentCardListModel(t, 0)
+	if m.payment.cardCursor != 0 {
+		t.Fatalf("default cursor = %d, want 0 ", m.payment.cardCursor)
+	}
+	newM, cmd := m.PaymentUpdate(keyEnter())
+	if newM.payment.view != 2 {
+		t.Fatalf("payment.view = %d, want 2 (browser flow)", newM.payment.view)
+	}
+	if newM.payment.form != nil {
+		t.Fatalf("payment.form must be nil; ssh inline form is dormant")
+	}
+	if cmd == nil {
+		t.Fatalf("expected collectCardCmd, got nil")
+	}
+}

pkg/tui/refund.go

@@ -129,7 +129,7 @@ func (m Model) RefundUpdate(msg tea.Msg) (Model, tea.Cmd) {
 			state.form = f
 		}
 		if state.form.State == huh.StateCompleted {
-			state.form = m.buildRefundForm(state)
+			state.reason = state.form.GetString("reason")
 			return m, m.setRefundFocus(state, refundFocusMessage)
 		}
 		return m, cmd
@@ -335,7 +335,7 @@ func (m Model) renderRefundTextarea(state *refundState) string {
 	}
 
 	wrapper := lipgloss.NewStyle().
-		Border(lipgloss.ThickBorder()).
+		Border(lipgloss.RoundedBorder()).
 		BorderForeground(border)
 
 	contentWidth := m.refundContentWidth()

pkg/utils/response.go

@@ -8,8 +8,8 @@ import (
 
 // SuccessResponse represents a successful API response
 type SuccessResponse struct {
-	Success bool        `json:"success"`
-	Data    interface{} `json:"data"`
+	Success bool `json:"success"`
+	Data    any  `json:"data"`
 }
 
 // ErrorResponse represents an error API response
@@ -20,13 +20,13 @@ type ErrorResponse struct {
 
 // Error contains error details
 type Error 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"`
 }
 
 // RespondSuccess sends a successful JSON response
-func RespondSuccess(w http.ResponseWriter, statusCode int, data interface{}) {
+func RespondSuccess(w http.ResponseWriter, statusCode int, data any) {
 	w.Header().Set("Content-Type", "application/json")
 	w.WriteHeader(statusCode)
 
@@ -39,7 +39,7 @@ func RespondSuccess(w http.ResponseWriter, statusCode int, data interface{}) {
 }
 
 // RespondError sends an error JSON response
-func RespondError(w http.ResponseWriter, statusCode int, code, message string, details map[string]interface{}) {
+func RespondError(w http.ResponseWriter, statusCode int, code, message string, details map[string]any) {
 	w.Header().Set("Content-Type", "application/json")
 	w.WriteHeader(statusCode)
 

scripts/backups/01-log-tail.sh

@@ -0,0 +1,13 @@
+#!/usr/bin/env bash
+# Show last 20 lines of the cron log + its mtime. Cheapest "did it run" check.
+set -euo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+source "$SCRIPT_DIR/lib.sh"
+
+print_header "Backup log: mtime + last 20 lines"
+spinner_start "fetching log from $SSH_HOST..."
+ssh "$SSH_HOST" "
+  sudo stat -c 'Last modified: %y' '$BACKUP_LOG'
+  echo; sudo tail -20 '$BACKUP_LOG'
+"
+spinner_stop

scripts/backups/02-snapshots.sh

@@ -0,0 +1,14 @@
+#!/usr/bin/env bash
+# List every restic snapshot with timestamps and tags.
+set -euo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+source "$SCRIPT_DIR/lib.sh"
+
+print_header "All restic snapshots"
+spinner_start "querying restic via SFTP..."
+ssh "$SSH_HOST" "
+  export RESTIC_PASSWORD_FILE='$RESTIC_PASSWORD_FILE'
+  export RESTIC_REPOSITORY='$RESTIC_REPO'
+  sudo -E restic -o sftp.args='-i $RESTIC_SSH_KEY' snapshots
+"
+spinner_stop

scripts/backups/03-check.sh

@@ -0,0 +1,21 @@
+#!/usr/bin/env bash
+# restic repo integrity check.
+#   ./03-check.sh         metadata only (~5s)
+#   ./03-check.sh --deep  + 10% data-pack re-read (~30s)
+set -euo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+source "$SCRIPT_DIR/lib.sh"
+
+EXTRA=""
+if [ "${1:-}" = "--deep" ]; then
+  EXTRA="--read-data-subset=10%"
+fi
+
+print_header "restic check ${EXTRA:-(metadata only)}"
+spinner_start "running restic check on $SSH_HOST..."
+ssh "$SSH_HOST" "
+  export RESTIC_PASSWORD_FILE='$RESTIC_PASSWORD_FILE'
+  export RESTIC_REPOSITORY='$RESTIC_REPO'
+  sudo -E restic -o sftp.args='-i $RESTIC_SSH_KEY' check $EXTRA
+"
+spinner_stop

scripts/backups/04-restore-verify.sh

@@ -0,0 +1,57 @@
+#!/usr/bin/env bash
+# Restore the latest snapshot to /tmp on the remote box, then:
+#   - PRAGMA integrity_check on the restored DB
+#   - row-count diff vs the live DB
+# Cleans up /tmp dir at the end.
+set -euo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+source "$SCRIPT_DIR/lib.sh"
+
+print_header "Restore latest snapshot and verify SQLite"
+spinner_start "restoring latest snapshot to /tmp on $SSH_HOST..."
+
+ssh "$SSH_HOST" \
+  "PWFILE='$RESTIC_PASSWORD_FILE' \
+   REPO='$RESTIC_REPO' \
+   KEY='$RESTIC_SSH_KEY' \
+   LIVE='$LIVE_DB' \
+   bash -s" <<'REMOTE'
+set -e
+DIR=/tmp/tshop-restore-test
+sudo rm -rf "$DIR" && sudo mkdir -p "$DIR"
+
+sudo -E RESTIC_PASSWORD_FILE="$PWFILE" RESTIC_REPOSITORY="$REPO" \
+  restic -o sftp.args="-i $KEY" restore latest --target "$DIR"
+
+DB=$(sudo find "$DIR" -name 'terminalshop.db' | head -1)
+if [ -z "$DB" ]; then
+  echo 'restored DB not found' >&2
+  exit 1
+fi
+
+echo
+echo '--- restored file ---'
+sudo stat -c '%y  %s bytes  %n' "$DB"
+
+echo
+echo '--- PRAGMA integrity_check ---'
+sudo sqlite3 "$DB" 'PRAGMA integrity_check;'
+
+echo
+echo '--- PRAGMA quick_check ---'
+sudo sqlite3 "$DB" 'PRAGMA quick_check;'
+
+echo
+echo '--- restored vs live row counts ---'
+printf '%-22s %10s %10s\n' table restored live
+for t in $(sudo sqlite3 "$DB" 'SELECT name FROM sqlite_master WHERE type="table";'); do
+  r=$(sudo sqlite3 "$DB" "SELECT COUNT(*) FROM \"$t\";")
+  l=$(sudo sqlite3 "$LIVE" "SELECT COUNT(*) FROM \"$t\";" 2>/dev/null || echo 'n/a')
+  printf '%-22s %10s %10s\n' "$t" "$r" "$l"
+done
+
+sudo rm -rf "$DIR"
+echo
+echo 'OK'
+REMOTE
+spinner_stop

scripts/backups/05-freshness.sh

@@ -0,0 +1,41 @@
+#!/usr/bin/env bash
+# Print latest snapshot age. Exit 0 if fresh, 1 if older than STALE_HOURS.
+set -euo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+source "$SCRIPT_DIR/lib.sh"
+
+print_header "Latest snapshot freshness"
+
+spinner_start "querying latest snapshot..."
+LATEST=$(ssh "$SSH_HOST" "
+  export RESTIC_PASSWORD_FILE='$RESTIC_PASSWORD_FILE'
+  export RESTIC_REPOSITORY='$RESTIC_REPO'
+  sudo -E restic -o sftp.args='-i $RESTIC_SSH_KEY' snapshots --json
+" | jq -r 'max_by(.time) | .time')
+spinner_stop
+
+if [ -z "$LATEST" ] || [ "$LATEST" = "null" ]; then
+  echo "ERROR: could not parse latest snapshot time" >&2
+  exit 2
+fi
+
+NOW=$(date -u +%s)
+# GNU date (Linux) first, then BSD date (macOS) as fallback.
+if THEN=$(date -u -d "$LATEST" +%s 2>/dev/null); then
+  :
+else
+  CLEAN=$(echo "$LATEST" | sed 's/\.[0-9]*Z$/Z/')
+  THEN=$(date -u -j -f "%Y-%m-%dT%H:%M:%SZ" "$CLEAN" +%s)
+fi
+
+AGE_HRS=$(( (NOW - THEN) / 3600 ))
+echo "Latest snapshot: $LATEST"
+echo "Age:             ${AGE_HRS}h"
+echo "Threshold:       ${STALE_HOURS}h"
+
+if [ "$AGE_HRS" -lt "$STALE_HOURS" ]; then
+  print_ok "snapshot within freshness window"
+else
+  print_fail "STALE — investigate"
+  exit 1
+fi

scripts/backups/06-lfs-direct.sh

@@ -0,0 +1,59 @@
+#!/usr/bin/env bash
+# Independent filesystem check on lfs-remote. No restic, no password needed.
+# Proves the repo dir exists, files are present, recent uploads landed,
+# and the backup partition has room.
+set -euo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+source "$SCRIPT_DIR/lib.sh"
+
+print_header "lfs-remote filesystem-level repo check"
+spinner_start "inspecting $LFS_HOST filesystem..."
+
+ssh "$LFS_HOST" "
+set -e
+REPO='$LFS_REPO_PATH'
+WARN_PCT=$LFS_DISK_WARN_PCT
+
+if [ ! -d \"\$REPO\" ]; then
+  echo 'ERROR: repo dir missing on lfs' >&2
+  exit 1
+fi
+
+echo '--- snapshot pointer count (one file per restic snapshot) ---'
+COUNT=\$(find \"\$REPO/snapshots\" -type f 2>/dev/null | wc -l)
+echo \"snapshots/: \$COUNT files\"
+
+echo
+echo '--- repo size on disk ---'
+du -sh \"\$REPO\"
+
+echo
+echo '--- recent uploads (files newer than 48h) ---'
+RECENT=\$(find \"\$REPO\" -type f -mtime -2 2>/dev/null | wc -l)
+echo \"files added in last 48h: \$RECENT\"
+if [ \"\$RECENT\" -eq 0 ]; then
+  echo 'WARN: no new files in last 48h' >&2
+fi
+
+echo
+echo '--- most recent snapshot pointer ---'
+LATEST=\$(ls -t \"\$REPO/snapshots\"/* 2>/dev/null | head -1)
+if [ -n \"\$LATEST\" ]; then
+  stat -c '%y  %n' \"\$LATEST\"
+else
+  echo 'WARN: no snapshot files found' >&2
+fi
+
+echo
+echo '--- disk usage ---'
+df -h \"\$REPO\"
+USED=\$(df --output=pcent \"\$REPO\" 2>/dev/null | tail -1 | tr -dc 0-9)
+if [ -n \"\$USED\" ] && [ \"\$USED\" -gt \"\$WARN_PCT\" ]; then
+  echo \"FAIL: backup partition \${USED}% full (threshold \${WARN_PCT}%)\" >&2
+  exit 1
+fi
+
+echo
+echo 'OK'
+"
+spinner_stop

scripts/backups/07-lfs-restic-check.sh

@@ -0,0 +1,38 @@
+#!/usr/bin/env bash
+# Independent restic check from the lfs-remote side. Reads repo via a
+# LOCAL filesystem path (not SFTP), so it proves the data is parseable
+# without any involvement from the prod box at restic level.
+#
+# Needs:
+#   - restic installed on lfs-remote (see scratchpkg port at /usr/ports/main/restic)
+#   - SSH access to both prod (to fetch the repo password) and lfs
+set -euo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+source "$SCRIPT_DIR/lib.sh"
+
+print_header "lfs-remote restic check (independent vantage point)"
+
+# Precondition: restic must be on lfs.
+if ! ssh "$LFS_HOST" 'command -v restic >/dev/null 2>&1'; then
+  echo 'ERROR: restic not in PATH on lfs-remote' >&2
+  echo "Install via scratchpkg, then re-run." >&2
+  exit 2
+fi
+
+# Pull restic password from prod (needs sudo on prod).
+spinner_start "fetching restic password from $SSH_HOST..."
+PW=$(ssh "$SSH_HOST" "sudo cat '$RESTIC_PASSWORD_FILE'")
+spinner_stop
+if [ -z "$PW" ]; then
+  echo 'ERROR: could not read restic password from prod' >&2
+  exit 2
+fi
+
+# Run restic against the LOCAL repo path on lfs. Password fed via stdin
+# so it never lands in argv or a file on lfs.
+spinner_start "running restic check from $LFS_HOST..."
+ssh "$LFS_HOST" "restic -r '$LFS_REPO_PATH' --password-file=/dev/stdin check" <<<"$PW"
+spinner_stop
+
+echo
+print_ok "lfs-side restic check passed"

scripts/backups/check-all.sh

@@ -0,0 +1,138 @@
+#!/usr/bin/env bash
+# Master runner. Executes every backup check in sequence.
+#   ./check-all.sh              stop on first failure; interactive menu when TTY
+#   ./check-all.sh --keep-going keep running after failures (no menu)
+#   ./check-all.sh --deep       use --deep on 03-check.sh
+#
+# When stdin and stdout are TTYs, a failed step opens a drill-down menu:
+#   [r]etry  [l]og  [u]nlock  [s]kip  [q]uit
+# Non-TTY (cron / piped) skips the menu and behaves like the old runner.
+set -uo pipefail
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+
+KEEP_GOING=0
+DEEP=0
+for arg in "$@"; do
+  case "$arg" in
+    --keep-going) KEEP_GOING=1 ;;
+    --deep)       DEEP=1 ;;
+    -h|--help)
+      echo "Usage: $0 [--keep-going] [--deep]"
+      echo "  --keep-going  don't stop on first failure, suppress interactive menu"
+      echo "  --deep        pass --deep to 03-check.sh (10% data re-read)"
+      exit 0
+      ;;
+    *)
+      echo "unknown flag: $arg" >&2
+      exit 2
+      ;;
+  esac
+done
+
+# Pull in config + color helpers (also gives us SSH_HOST + restic env for unlock).
+source "$SCRIPT_DIR/lib.sh"
+
+declare -a STEP_NAMES=()
+declare -a STEP_STATUS=()   # OK | FAIL
+FAIL=0
+
+prompt_after_fail() {
+  # returns 0=skip, 1=quit, 2=retry
+  local script="$1"
+  while :; do
+    printf '\n%sNext?%s [r]etry  [l]og  [u]nlock  [s]kip  [q]uit > ' "$C_BOLD" "$C_RESET"
+    local choice
+    read -r choice
+    case "$choice" in
+      r|R) return 2 ;;
+      l|L) "$SCRIPT_DIR/01-log-tail.sh"; echo ;;
+      u|U)
+        echo
+        ssh "$SSH_HOST" "
+          export RESTIC_PASSWORD_FILE='$RESTIC_PASSWORD_FILE'
+          export RESTIC_REPOSITORY='$RESTIC_REPO'
+          sudo -E restic -o sftp.args='-i $RESTIC_SSH_KEY' unlock
+        "
+        echo
+        ;;
+      s|S) return 0 ;;
+      q|Q) return 1 ;;
+      "")  ;;
+      *)   printf 'unknown: %s\n' "$choice" ;;
+    esac
+  done
+}
+
+run_step() {
+  local script="$1"; shift
+  echo
+  printf '%s########## %s %s ##########%s\n' "$C_CYAN$C_BOLD" "$script" "$*" "$C_RESET"
+
+  local attempts=0
+  while :; do
+    attempts=$((attempts + 1))
+    if "$SCRIPT_DIR/$script" "$@"; then
+      STEP_NAMES+=("$script")
+      STEP_STATUS+=("OK")
+      return 0
+    fi
+
+    printf '%sFAILED:%s %s\n' "$C_RED$C_BOLD" "$C_RESET" "$script" >&2
+
+    if [ -t 0 ] && [ -t 1 ] && [ "$KEEP_GOING" -eq 0 ]; then
+      prompt_after_fail "$script"
+      case "$?" in
+        0) STEP_NAMES+=("$script"); STEP_STATUS+=("FAIL"); FAIL=$((FAIL + 1)); return 0 ;;
+        1) STEP_NAMES+=("$script"); STEP_STATUS+=("FAIL"); FAIL=$((FAIL + 1)); print_summary; exit 1 ;;
+        2) echo
+           printf '%s>>>>>> retry %s (attempt %d) <<<<<<%s\n' "$C_CYAN$C_BOLD" "$script" $((attempts + 1)) "$C_RESET"
+           continue ;;
+      esac
+    fi
+
+    # non-interactive path
+    STEP_NAMES+=("$script")
+    STEP_STATUS+=("FAIL")
+    FAIL=$((FAIL + 1))
+    if [ "$KEEP_GOING" -eq 0 ]; then
+      print_summary
+      exit 1
+    fi
+    return 0
+  done
+}
+
+print_summary() {
+  echo
+  printf '%s===============================================%s\n' "$C_CYAN$C_BOLD" "$C_RESET"
+  printf '   %-28s %s\n' "Script" "Result"
+  printf '   %-28s %s\n' "----------------------------" "--------"
+  local i
+  for i in "${!STEP_NAMES[@]}"; do
+    local name="${STEP_NAMES[$i]}"
+    local status="${STEP_STATUS[$i]}"
+    local color sym
+    case "$status" in
+      OK)   color="$C_GREEN"; sym="✓ OK"   ;;
+      FAIL) color="$C_RED"  ; sym="✗ FAIL" ;;
+    esac
+    printf '   %-28s %s%s%s\n' "$name" "$color" "$sym" "$C_RESET"
+  done
+  printf '%s===============================================%s\n' "$C_CYAN$C_BOLD" "$C_RESET"
+  if [ "$FAIL" -eq 0 ]; then
+    printf '%sAll checks passed.%s\n' "$C_GREEN$C_BOLD" "$C_RESET"
+  else
+    printf '%s%d check(s) failed.%s\n' "$C_RED$C_BOLD" "$FAIL" "$C_RESET"
+  fi
+}
+
+run_step 01-log-tail.sh
+run_step 02-snapshots.sh
+if [ "$DEEP" -eq 1 ]; then run_step 03-check.sh --deep; else run_step 03-check.sh; fi
+run_step 04-restore-verify.sh
+run_step 05-freshness.sh
+run_step 06-lfs-direct.sh
+run_step 07-lfs-restic-check.sh
+
+print_summary
+[ "$FAIL" -eq 0 ] || exit 1

scripts/backups/config.env.example

@@ -0,0 +1,28 @@
+# Backup verification config.
+# Copy to config.env (gitignored) and fill in your real values.
+#
+#   cp config.env.example config.env
+#   $EDITOR config.env
+
+# SSH alias for the prod box (resolved via ~/.ssh/config).
+SSH_HOST="ubuntu-helsinki"
+
+# Restic repository URL. Format: sftp:HOST:PATH
+# HOST is the Tailscale name of the backup target box.
+RESTIC_REPO="sftp:YOUR_TAILNET_HOST.ts.net:/root/backups/tshop"
+
+# Paths on the REMOTE prod box (not your laptop).
+RESTIC_PASSWORD_FILE="/root/.restic-password"
+RESTIC_SSH_KEY="/root/.ssh/tshop-backup"
+BACKUP_LOG="/var/log/backup-tshop.log"
+LIVE_DB="/root/terminalShop/data/terminalshop.db"
+
+# Freshness alert threshold (hours). 24h cron + 4h slop = 28.
+STALE_HOURS="28"
+
+# lfs-remote = the box that RECEIVES the backups.
+# Used by 06-lfs-direct.sh and 07-lfs-restic-check.sh for out-of-band checks.
+LFS_HOST="lfs-remote"
+LFS_REPO_PATH="/root/backups/tshop"
+# 06 fails if the backup partition is more full than this percent.
+LFS_DISK_WARN_PCT="80"

scripts/backups/lib.sh

@@ -0,0 +1,65 @@
+#!/usr/bin/env bash
+# Shared loader for the backup verification scripts.
+# Each script should: source "$SCRIPT_DIR/lib.sh"
+
+SCRIPT_DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" && pwd )"
+
+if [ ! -f "$SCRIPT_DIR/config.env" ]; then
+  echo "ERROR: $SCRIPT_DIR/config.env missing." >&2
+  echo "Run: cp $SCRIPT_DIR/config.env.example $SCRIPT_DIR/config.env" >&2
+  exit 1
+fi
+
+# shellcheck source=/dev/null
+source "$SCRIPT_DIR/config.env"
+
+# ANSI colors. Emit only when stdout is a TTY and NO_COLOR is unset.
+if [ -t 1 ] && [ -z "${NO_COLOR:-}" ]; then
+  C_RED=$'\033[1;31m'
+  C_GREEN=$'\033[1;32m'
+  C_YELLOW=$'\033[1;33m'
+  C_BLUE=$'\033[1;34m'
+  C_CYAN=$'\033[1;36m'
+  C_BOLD=$'\033[1m'
+  C_RESET=$'\033[0m'
+else
+  C_RED=""; C_GREEN=""; C_YELLOW=""; C_BLUE=""; C_CYAN=""; C_BOLD=""; C_RESET=""
+fi
+
+print_header() { printf '\n%s=== %s ===%s\n' "$C_CYAN" "$1" "$C_RESET"; }
+print_ok()     { printf '%sOK%s%s\n'    "$C_GREEN"  "$C_RESET" "${1:+ — $1}"; }
+print_fail()   { printf '%sFAIL%s%s\n'  "$C_RED"    "$C_RESET" "${1:+ — $1}" >&2; }
+print_warn()   { printf '%sWARN%s%s\n'  "$C_YELLOW" "$C_RESET" "${1:+ — $1}" >&2; }
+print_info()   { printf '%s%s%s\n'      "$C_BLUE"   "$1"       "$C_RESET"; }
+
+# Spinner: shows a rotating braille char while a foreground command runs.
+# Use as a pair around the silent/blocking call:
+#   spinner_start "fetching log..."
+#   ssh ...
+#   spinner_stop
+# Auto-skips when stdout isn't a TTY (cron / piped). Real output from the
+# wrapped command will visually overwrite the spinner — by design.
+SPINNER_PID=""
+spinner_start() {
+  [ -t 1 ] && [ -z "${NO_COLOR:-}" ] || return 0
+  local msg="${1:-working}"
+  (
+    trap 'exit 0' TERM
+    local chars=('⠋' '⠙' '⠹' '⠸' '⠼' '⠴' '⠦' '⠧' '⠇' '⠏')
+    local i=0
+    while :; do
+      i=$(( (i + 1) % ${#chars[@]} ))
+      printf '\r%s%s%s %s' "$C_CYAN" "${chars[$i]}" "$C_RESET" "$msg"
+      sleep 0.08
+    done
+  ) &
+  SPINNER_PID=$!
+  disown "$SPINNER_PID" 2>/dev/null || true
+}
+spinner_stop() {
+  [ -n "$SPINNER_PID" ] || return 0
+  kill "$SPINNER_PID" 2>/dev/null || true
+  wait "$SPINNER_PID" 2>/dev/null || true
+  printf '\r\033[K'
+  SPINNER_PID=""
+}