diff --git a/apps/edr-passenger-api/src/common/utils/payment-deadline.utils.ts b/apps/edr-passenger-api/src/common/utils/payment-deadline.utils.ts
index e125bb0bf..8c391aef1 100644
--- a/apps/edr-passenger-api/src/common/utils/payment-deadline.utils.ts
+++ b/apps/edr-passenger-api/src/common/utils/payment-deadline.utils.ts
@@ -13,11 +13,17 @@ export const MAX_PAYMENT_HOURS = 2;
 export const CUTOFF_MINUTES = 30;
 
 /**
- * payment_deadline = MIN(booking_time + MAX_PAYMENT_HOURS, segment_departure - checkinMinutes)
- *
- * checkinMinutes defaults to CUTOFF_MINUTES but callers should pass the route-level
- * checkinMinutesBefore so that each route's own window is respected.
+ * How long a passenger is given to finish one provider payment session, once opened.
+ * 5 minutes of actual paying (redirect → PIN/OTP → provider callback) + 1 minute of slack.
  */
+export const PAYMENT_SESSION_MINUTES = 6;
+
+
+export const MIN_PAYMENT_WINDOW_MINUTES = 7;
+
+export const PAYMENT_SETTLE_MARGIN_SECONDS = 60;
+
+
 export function computePaymentDeadline(
   createdAt: Date,
   departureAt: Date,
@@ -27,3 +33,19 @@ export function computePaymentDeadline(
   const cutoffDeadline = new Date(departureAt.getTime() - checkinMinutes * 60 * 1000);
   return maxDeadline < cutoffDeadline ? maxDeadline : cutoffDeadline;
 }
+
+
+export function canOpenPaymentSession(
+  paymentDeadline: Date,
+  now: Date = new Date(),
+): boolean {
+  return paymentDeadline.getTime() - now.getTime() >= MIN_PAYMENT_WINDOW_MINUTES * 60 * 1000;
+}
+
+export function computePaymentSessionExpiry(
+  paymentDeadline: Date,
+  now: Date = new Date(),
+): Date {
+  const sessionEnd = new Date(now.getTime() + PAYMENT_SESSION_MINUTES * 60 * 1000);
+  return sessionEnd < paymentDeadline ? sessionEnd : paymentDeadline;
+}
diff --git a/apps/edr-passenger-api/src/modules/payments/payments.dto.ts b/apps/edr-passenger-api/src/modules/payments/payments.dto.ts
index dc389e5a1..1d033e5ff 100644
--- a/apps/edr-passenger-api/src/modules/payments/payments.dto.ts
+++ b/apps/edr-passenger-api/src/modules/payments/payments.dto.ts
@@ -154,6 +154,10 @@ export class InitiateResponseDto {
   @ApiPropertyOptional({ type: ClientActionDto })
   clientAction?: ClientActionDto;
   @ApiPropertyOptional() merchantOrderId?: string;
+  /** When this payment session stops being offered — PAYMENT_SESSION_MINUTES from initiation, capped at paymentDeadline. Drives the client-side countdown. */
+  @ApiPropertyOptional() sessionExpiresAt?: string;
+  /** The booking's payment deadline: after it, the booking is auto-cancelled. */
+  @ApiPropertyOptional() paymentDeadline?: string;
 }
 
 export class IntentStatusDto {
diff --git a/apps/edr-passenger-api/src/modules/payments/payments.service.spec.ts b/apps/edr-passenger-api/src/modules/payments/payments.service.spec.ts
index 8c4edf083..186383335 100644
--- a/apps/edr-passenger-api/src/modules/payments/payments.service.spec.ts
+++ b/apps/edr-passenger-api/src/modules/payments/payments.service.spec.ts
@@ -16,6 +16,11 @@ import {
   ProviderMethod,
   ProviderPaymentStatus,
 } from "@edr/types";
+import {
+  MAX_PAYMENT_HOURS,
+  MIN_PAYMENT_WINDOW_MINUTES,
+  PAYMENT_SESSION_MINUTES,
+} from "../../common/utils/payment-deadline.utils";
 
 describe("PaymentsService", () => {
   let service: PaymentsService;
@@ -163,6 +168,69 @@ describe("PaymentsService", () => {
       ).rejects.toThrow(BadRequestException);
     });
 
+    /**
+     * A booking whose payment deadline lands exactly `minutesLeft` from now: the deadline is
+     * MIN(createdAt + MAX_PAYMENT_HOURS, departure - checkin), so back-date createdAt and keep
+     * departure far away. Derived from MAX_PAYMENT_HOURS so the test survives changes to it.
+     */
+    const bookingWithDeadlineIn = (minutesLeft: number) => ({
+      ...mockBooking,
+      createdAt: new Date(
+        Date.now() - (MAX_PAYMENT_HOURS * 60 - minutesLeft) * 60 * 1000,
+      ),
+      originStationId: null,
+      schedule: {
+        departureAt: new Date(Date.now() + 10 * 60 * 60 * 1000),
+        stopTimes: [],
+        route: null,
+      },
+    });
+
+    it("should refuse to open a provider session that cannot finish before auto-cancel", async () => {
+      // 2 minutes left — the real incident: the session was opened, the provider captured the
+      // money, and the auto-cancel cron had already cancelled the booking by then.
+      mockPrisma.booking.findUnique.mockResolvedValue(bookingWithDeadlineIn(2));
+
+      await expect(
+        service.initiatePayment({
+          bookingId: "booking-1",
+          method: "TELEBIRR" as any,
+        }),
+      ).rejects.toThrow(BadRequestException);
+
+      // Nothing may reach the provider — no session, no capture, no orphan payment.
+      expect(mockPaymentClient.initiate).not.toHaveBeenCalled();
+    });
+
+    it("should open a session and report its expiry when the window is wide enough", async () => {
+      const minutesLeft = MIN_PAYMENT_WINDOW_MINUTES + 3;
+      mockPrisma.booking.findUnique.mockResolvedValue(
+        bookingWithDeadlineIn(minutesLeft),
+      );
+      mockPaymentClient.initiate.mockResolvedValue(
+        requiresActionSnapshot(ProviderMethod.TELEBIRR),
+      );
+      mockPrisma.paymentIntent.upsert.mockResolvedValue({
+        id: "intent-1",
+        status: PaymentIntentStatus.REQUIRES_ACTION,
+        merchantOrderId: "PSG-MERCH-123",
+      });
+
+      const result = await service.initiatePayment({
+        bookingId: "booking-1",
+        method: "TELEBIRR" as any,
+      });
+
+      expect(mockPaymentClient.initiate).toHaveBeenCalled();
+      // Session ends PAYMENT_SESSION_MINUTES from now — before the deadline, not at it.
+      const sessionMs =
+        new Date(result.sessionExpiresAt!).getTime() - Date.now();
+      expect(sessionMs).toBeLessThanOrEqual(PAYMENT_SESSION_MINUTES * 60 * 1000);
+      expect(new Date(result.sessionExpiresAt!).getTime()).toBeLessThan(
+        new Date(result.paymentDeadline!).getTime(),
+      );
+    });
+
     it("should initiate a provider payment through the payment microservice", async () => {
       mockPrisma.booking.findUnique.mockResolvedValue(mockBooking);
       mockPaymentClient.initiate.mockResolvedValue(
diff --git a/apps/edr-passenger-api/src/modules/payments/payments.service.ts b/apps/edr-passenger-api/src/modules/payments/payments.service.ts
index 14e48dce5..2b1b14cf1 100644
--- a/apps/edr-passenger-api/src/modules/payments/payments.service.ts
+++ b/apps/edr-passenger-api/src/modules/payments/payments.service.ts
@@ -29,7 +29,13 @@ import {
   MarkPaidResponseDto,
   BillQueryResponseDto,
 } from "./internal-payments.dto";
-import { computePaymentDeadline } from "../../common/utils/payment-deadline.utils";
+import {
+  computePaymentDeadline,
+  computePaymentSessionExpiry,
+  canOpenPaymentSession,
+  MIN_PAYMENT_WINDOW_MINUTES,
+  PAYMENT_SETTLE_MARGIN_SECONDS,
+} from "../../common/utils/payment-deadline.utils";
 import {
   PaymentClientService,
   PaymentDiagnostic,
@@ -260,6 +266,27 @@ export class PaymentsService {
       return this.initiateWalletPayment(booking);
     }
 
+    // Refuse to open a provider session that cannot finish before auto-cancel. Everything below
+    // this point hands the passenger off to an external provider (redirect/HPP/OTP), which takes
+    // minutes; TasksService cancels the booking the first cron tick after its payment deadline.
+    // Opening a session with less than MIN_PAYMENT_WINDOW_MINUTES left produces the worst possible
+    // outcome — the provider captures the money and the booking is already CANCELLED when the
+    // capture lands. WALLET is exempt (returned above): it is an instant internal balance debit.
+    const paymentDeadline = await this.computeBookingPaymentDeadline(booking.id);
+    const sessionExpiresAt = paymentDeadline
+      ? computePaymentSessionExpiry(paymentDeadline)
+      : undefined;
+    if (paymentDeadline && !canOpenPaymentSession(paymentDeadline)) {
+      const remainingMs = paymentDeadline.getTime() - Date.now();
+      throw new BadRequestException(
+        remainingMs <= 0
+          ? "The payment window for this booking has expired. Please make a new booking."
+          : `Too little time is left to start a payment (${Math.ceil(remainingMs / 60000)} minute(s) ` +
+            `until this booking expires; at least ${MIN_PAYMENT_WINDOW_MINUTES} are required). ` +
+            `Please make a new booking.`,
+      );
+    }
+
     // Free method changes: no reuse/blocking. Every initiate opens a fresh provider session; the
     // single passenger projection row (upserted by bookingId below) tracks the latest session.
     // Confirm-once is enforced when a payment succeeds (finalizePaymentSuccess), not here.
@@ -317,9 +344,7 @@ export class PaymentsService {
       payerName =
         booking.seats.find((s) => s.leg === 1)?.passengerName ??
         booking.seats[0]?.passengerName;
-      expiresAt = (
-        await this.computeBookingPaymentDeadline(booking.id)
-      )?.toISOString();
+      expiresAt = paymentDeadline?.toISOString();
     }
 
     const snapshot = await this.paymentClient.initiate({
@@ -350,7 +375,11 @@ export class PaymentsService {
         where: { id: intent.id },
       });
     }
-    return this.formatIntentResponse(intent);
+    return {
+      ...this.formatIntentResponse(intent),
+      sessionExpiresAt: sessionExpiresAt?.toISOString(),
+      paymentDeadline: paymentDeadline?.toISOString(),
+    };
   }
 
   /**
@@ -436,8 +465,15 @@ export class PaymentsService {
     if (booking.status !== "PENDING_PAYMENT") {
       return { ...base, stillPayable: false, reason: "NOT_PAYABLE" };
     }
+    // A CBE debit confirmed now lands in seconds, so this doesn't need the full
+    // MIN_PAYMENT_WINDOW_MINUTES that opening a session does — but it must not be confirmed so
+    // close to the deadline that the auto-cancel cron cancels the booking before the capture is
+    // registered. Refusing here is what keeps CBE from debiting a passenger for a dead booking.
     const deadline = await this.computeBookingPaymentDeadline(booking.id);
-    if (deadline && deadline.getTime() < Date.now()) {
+    if (
+      deadline &&
+      deadline.getTime() - PAYMENT_SETTLE_MARGIN_SECONDS * 1000 < Date.now()
+    ) {
       return { ...base, stillPayable: false, reason: "EXPIRED" };
     }
     return { ...base, stillPayable: true, reason: null };
diff --git a/packages/payment-providers/src/providers/dmoney/dmoney.provider.ts b/packages/payment-providers/src/providers/dmoney/dmoney.provider.ts
index 51e90381b..3af351e32 100644
--- a/packages/payment-providers/src/providers/dmoney/dmoney.provider.ts
+++ b/packages/payment-providers/src/providers/dmoney/dmoney.provider.ts
@@ -353,7 +353,7 @@ export class DMoneyProvider implements PaymentProvider {
     return this.config.get<string>("dmoney.returnUrl") ?? "";
   }
   private get timeoutExpress(): string {
-    return this.config.get<string>("dmoney.timeoutExpress") ?? "120m";
+    return this.config.get<string>("dmoney.timeoutExpress") ?? "5m";
   }
   private get language(): string {
     return this.config.get<string>("dmoney.language") ?? "en";