diff --git a/api/handlers/webhook.go b/api/handlers/webhook.go
index 357b669..ba80a57 100644
--- a/api/handlers/webhook.go
+++ b/api/handlers/webhook.go
@@ -279,7 +279,11 @@ func (h *WebhookHandler) HandleShippo(w http.ResponseWriter, r *http.Request) {
 
 	if payload.Event != "track_updated" {
 		webhookLog().Info("shippo webhook: ignoring no-tracking event", "event", payload.Event)
-		w.WriteHeader(http.StatusOK)
+		writeShippoResponse(w, map[string]any{
+			"received": true,
+			"skipped":  "non-tracking event",
+			"event":    payload.Event,
+		})
 		return
 	}
 
@@ -288,7 +292,11 @@ func (h *WebhookHandler) HandleShippo(w http.ResponseWriter, r *http.Request) {
 		webhookLog().Warn("shippo webhook: unrecognized status, skipping",
 			"status", payload.Data.TrackingStatus.Status,
 			"tracking_number", payload.Data.TrackingNumber)
-		w.WriteHeader(http.StatusOK)
+		writeShippoResponse(w, map[string]any{
+			"received":   true,
+			"skipped":    "unrecognized status",
+			"raw_status": payload.Data.TrackingStatus.Status,
+		})
 		return
 	}
 
@@ -297,12 +305,21 @@ func (h *WebhookHandler) HandleShippo(w http.ResponseWriter, r *http.Request) {
 	if err := db.Where("tracking_number = ?", payload.Data.TrackingNumber).First(&order).Error; err != nil {
 		webhookLog().Warn("shippo webhook: order not found",
 			"tracking_number", payload.Data.TrackingNumber)
-		w.WriteHeader(http.StatusOK)
+		writeShippoResponse(w, map[string]any{
+			"received":        true,
+			"skipped":         "order not found",
+			"tracking_number": payload.Data.TrackingNumber,
+		})
 		return
 	}
 
 	if order.TrackingStatusUpdatedAt != nil && !payload.Data.TrackingStatus.StatusDate.After(*order.TrackingStatusUpdatedAt) {
-		w.WriteHeader(http.StatusOK)
+		writeShippoResponse(w, map[string]any{
+			"received":                true,
+			"skipped":                 "stale status_date",
+			"order_id":                order.ID,
+			"current_tracking_status": string(order.TrackingStatus),
+		})
 		return
 	}
 
@@ -332,7 +349,15 @@ func (h *WebhookHandler) HandleShippo(w http.ResponseWriter, r *http.Request) {
 	if deliveredTransition {
 		audit.OrderDelivered(order.ID, payload.Data.TrackingNumber)
 	}
-	w.WriteHeader(http.StatusOK)
+	writeShippoResponse(w, map[string]any{
+		"received":                 true,
+		"order_id":                 order.ID,
+		"tracking_status":          string(newStatus),
+		"previous_tracking_status": string(previousTrackingStatus),
+		"lifecycle_status":         string(order.Status),
+		"delivered_transition":     deliveredTransition,
+		"status_details":           payload.Data.TrackingStatus.StatusDetails,
+	})
 }
 
 func mapShippoStatus(s string) (models.TrackingStatus, bool) {
@@ -352,3 +377,9 @@ func mapShippoStatus(s string) (models.TrackingStatus, bool) {
 	}
 	return models.TrackingStatusUnknown, false
 }
+
+func writeShippoResponse(w http.ResponseWriter, payload map[string]any) {
+	w.Header().Set("Content-Type", "application/json")
+	w.WriteHeader(http.StatusOK)
+	_ = json.NewEncoder(w).Encode(payload)
+}
diff --git a/pkg/models/order_display.go b/pkg/models/order_display.go
index 2f68c6b..5a21f9e 100644
--- a/pkg/models/order_display.go
+++ b/pkg/models/order_display.go
@@ -31,16 +31,16 @@ func (order *Order) DisplayState() string {
 	case OrderStatusShipped:
 		switch order.TrackingStatus {
 		case TrackingStatusTransit:
-			return "Shipped * in transit"
+			return "In Transit"
 		case TrackingStatusFailure:
-			return "Shipped * delivery issue"
+			return "Delivery Issue"
 		case TrackingStatusReturned:
-			return "Shipped * returned to sender"
+			return "Returned to Sender"
 		case TrackingStatusDelivered:
 			// Webhook hasn't promoted Status yet, trust tracking
 			return "Delivered"
 		}
-		return "Shipped"
+		return "Label Created"
 	case OrderStatusDelivered:
 		return "Delivered"
 	case OrderStatusCancelled:
diff --git a/pkg/models/order_display_test.go b/pkg/models/order_display_test.go
index 02a75f6..d81d63e 100644
--- a/pkg/models/order_display_test.go
+++ b/pkg/models/order_display_test.go
@@ -13,10 +13,11 @@ func TestOrderDisplayState(t *testing.T) {
 		{"paid no tracking", Order{Status: OrderStatusPaid}, "Paid * awaiting label", DisplayKindAccent},
 		{"paid with tracking, no event", Order{Status: OrderStatusPaid, TrackingNumber: "12999"}, "Paid", DisplayKindAccent},
 		{"Paid pre-transit", Order{Status: OrderStatusPaid, TrackingNumber: "12999", TrackingStatus: TrackingStatusPreTransit}, "Paid * ready to ship", DisplayKindAccent},
-		{"shipped no tracking event", Order{Status: OrderStatusShipped}, "Shipped", DisplayKindBrand},
-		{"shipped in transit", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusTransit}, "Shipped * in transit", DisplayKindBrand},
-		{"shipped failure", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusFailure}, "Shipped * delivery issue", DisplayKindWarning},
-		{"shipped returned", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusReturned}, "Shipped * returned to sender", DisplayKindWarning},
+		{"shipped no tracking event", Order{Status: OrderStatusShipped}, "Label Created", DisplayKindBrand},
+		{"shipped pre-transit", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusPreTransit}, "Label Created", DisplayKindBrand},
+		{"shipped in transit", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusTransit}, "In Transit", DisplayKindBrand},
+		{"shipped failure", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusFailure}, "Delivery Issue", DisplayKindWarning},
+		{"shipped returned", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusReturned}, "Returned to Sender", DisplayKindWarning},
 		{"shipped tracking-delivered (webhook lag)", Order{Status: OrderStatusShipped, TrackingStatus: TrackingStatusDelivered}, "Delivered", DisplayKindSuccess},
 		{"delivered", Order{Status: OrderStatusDelivered}, "Delivered", DisplayKindSuccess},
 		{"cancelled", Order{Status: OrderStatusCancelled}, "Cancelled", DisplayKindError},
diff --git a/pkg/tui/account_orders.go b/pkg/tui/account_orders.go
index 98b8beb..e03162b 100644
--- a/pkg/tui/account_orders.go
+++ b/pkg/tui/account_orders.go
@@ -104,6 +104,10 @@ func (m Model) buildOrderDetailView(order models.Order, _ int) string {
 	b.WriteString(labelStyle.Render("Status:  "))
 	b.WriteString(m.displayStyle(order.DisplayKind()).Render(order.DisplayState()))
 	b.WriteString("\n")
+	if order.TrackingStatusDetails != "" {
+		b.WriteString(dimStyle.Render("         " + order.TrackingStatusDetails))
+		b.WriteString("\n")
+	}
 	b.WriteString(labelStyle.Render("Date:    "))
 	b.WriteString(valueStyle.Render(order.CreatedAt.Format("Jan 02 2006 3:04 PM")))
 	b.WriteString("\n\n")