diff --git a/apps/edr-freight-web/portal/src/pages/bookings/booking-display.tsx b/apps/edr-freight-web/portal/src/pages/bookings/booking-display.tsx
index ec5abad1b..7dc1109eb 100644
--- a/apps/edr-freight-web/portal/src/pages/bookings/booking-display.tsx
+++ b/apps/edr-freight-web/portal/src/pages/bookings/booking-display.tsx
@@ -145,12 +145,38 @@ export function paymentStatusLabel(status?: string | null): string {
 }
 
 /**
- * Payment status pill. Once the booking's own lifecycle status has moved past
- * payment (PAID or later — stage ≥ 3 in STATUS_CONFIG), payment is a settled
- * fact: show "Paid" even if a stale/lagging `paymentStatus` value says
- * otherwise, rather than surface a contradictory "Paid booking, pending
- * payment" row.
+ * Booking statuses that are only reachable at or after the payment gate.
+ * Settlement writes `status` and `paymentStatus` in one transaction
+ * (booking-invoice.service.ts `advanceBookingOnPayment`), so these are a
+ * backstop for a stale/lagging `paymentStatus` — not the primary signal.
  */
+const PAID_OR_LATER_STATUSES = new Set([
+  "PAID",
+  "TRUCK_ASSIGNED",
+  "IN_TRANSIT",
+  "ARRIVED",
+  "COMPLETED",
+]);
+
+/**
+ * Payment status pill. `paymentStatus` is authoritative; the status set above
+ * only covers a lagging read, so a booking past the payment gate never shows a
+ * contradictory "Paid booking, pending payment" row.
+ *
+ * Note the set is explicit rather than derived from `STATUS_CONFIG.stage` —
+ * stage is a portal timeline grouping, and stage 3 lumps pre-payment clearance
+ * statuses (AWAITING_DOCUMENTS, CLEARANCE_READY, SIGNED_CUSTOMER, OPERATION_*)
+ * in with genuinely post-payment ones, which made every freshly initiated
+ * contract booking render as "Paid".
+ */
+export function effectivePaymentStatus(
+  status?: string | null,
+  bookingStatus?: string | null,
+): string | null | undefined {
+  const settled = bookingStatus ? PAID_OR_LATER_STATUSES.has(bookingStatus) : false;
+  return settled ? "PAID" : status;
+}
+
 export function PaymentBadge({
   status,
   bookingStatus,
@@ -158,8 +184,7 @@ export function PaymentBadge({
   status?: string | null;
   bookingStatus?: string | null;
 }) {
-  const settled = bookingStatus ? (STATUS_CONFIG[bookingStatus]?.stage ?? 0) >= 3 : false;
-  const effective = settled ? "PAID" : status;
+  const effective = effectivePaymentStatus(status, bookingStatus);
   if (!effective) return <Text fz={13} c="dimmed">—</Text>;
   return (
     <Badge
diff --git a/apps/edr-freight-web/portal/src/pages/bookings/payment-badge.test.ts b/apps/edr-freight-web/portal/src/pages/bookings/payment-badge.test.ts
new file mode 100644
index 000000000..658ad31a6
--- /dev/null
+++ b/apps/edr-freight-web/portal/src/pages/bookings/payment-badge.test.ts
@@ -0,0 +1,35 @@
+import { describe, expect, it } from "vitest";
+
+import { effectivePaymentStatus } from "./booking-display";
+
+describe("effectivePaymentStatus", () => {
+  it("keeps PENDING for pre-payment statuses", () => {
+    // Regression: these all sit at STATUS_CONFIG stage 3, so the old
+    // `stage >= 3` heuristic rendered every freshly initiated contract
+    // booking as "Paid".
+    for (const s of [
+      "AWAITING_DOCUMENTS",
+      "DOCUMENTS_UNDER_REVIEW",
+      "CLEARANCE_READY",
+      "SIGNED_CUSTOMER",
+      "FULLY_EXECUTED",
+      "SELECTED_FOR_BATCH",
+      "OPERATION_REQUEST_PENDING",
+      "PNR_GENERATED",
+    ]) {
+      expect(effectivePaymentStatus("PENDING", s)).toBe("PENDING");
+    }
+  });
+
+  it("shows PAID once the booking is at or past the payment gate", () => {
+    for (const s of ["PAID", "TRUCK_ASSIGNED", "IN_TRANSIT", "ARRIVED", "COMPLETED"]) {
+      expect(effectivePaymentStatus("PENDING", s)).toBe("PAID");
+    }
+  });
+
+  it("passes the real payment status through when the booking status is absent", () => {
+    expect(effectivePaymentStatus("PAID", null)).toBe("PAID");
+    expect(effectivePaymentStatus("FAILED", undefined)).toBe("FAILED");
+    expect(effectivePaymentStatus(null, null)).toBeNull();
+  });
+});