diff --git a/apps/edr-freight-api/src/modules/billing/billing.service.ts b/apps/edr-freight-api/src/modules/billing/billing.service.ts
index ab6b2f8c8..a334b5e28 100644
--- a/apps/edr-freight-api/src/modules/billing/billing.service.ts
+++ b/apps/edr-freight-api/src/modules/billing/billing.service.ts
@@ -957,7 +957,7 @@ export class BillingService {
       returnUrl: opts.returnUrl,
       failureUrl: opts.failureUrl,
     });
-
+//
     // Link the intent to the invoice BEFORE any settlement can correlate against it.
     await this.dataSource
       .getRepository(Invoice)
diff --git a/apps/edr-freight-api/src/modules/train-scheduling/train-scheduling.service.ts b/apps/edr-freight-api/src/modules/train-scheduling/train-scheduling.service.ts
index 240f7071f..265f9e676 100644
--- a/apps/edr-freight-api/src/modules/train-scheduling/train-scheduling.service.ts
+++ b/apps/edr-freight-api/src/modules/train-scheduling/train-scheduling.service.ts
@@ -20,6 +20,7 @@ import { DataSource, EntityManager, In, IsNull, Not } from 'typeorm';
 import { BookingsRepository } from '../bookings/bookings.repository';
 import { Booking } from '../bookings/entities/booking.entity';
 import { BookingContainer } from '../bookings/entities/booking-container.entity';
+import { ClearanceMilestone } from '../contracts/entities/clearance-milestone.entity';
 import { Container } from '../container-management/entities/container.entity';
 import { Locomotive } from '../locomotives/entities/locomotive.entity';
 import { LocomotivesRepository } from '../locomotives/locomotives.repository';
@@ -1168,12 +1169,47 @@ export class TrainSchedulingService {
       notes: dto.notes ?? operation.notes ?? null,
     });
 
+    await this.completeGatepassMilestoneForSchedule(scheduleId, securedAt);
+
     console.log(
       `[NOTIFY] Gate pass secured for train ${schedule.trainNumber ?? schedule.id}; Djibouti Port entry is allowed.`,
     );
     return this.getImportDjiboutiOperation(schedule.id);
   }
 
+  /**
+   * Bridge write: also flips the legacy clearance-side GATEPASS_GRANTED
+   * milestone for every customs booking on this schedule, so contract/booking
+   * clearance views still reading that milestone (older deployed builds) see
+   * the gate pass as done. Drop once every clearance-api deployment reads
+   * ImportDjiboutiOperation.gatepassGrantedAt directly.
+   */
+  private async completeGatepassMilestoneForSchedule(
+    scheduleId: string,
+    securedAt: Date,
+  ): Promise<void> {
+    const bookings = await this.dataSource.getRepository(Booking).find({
+      where: { trainScheduleId: scheduleId, customsClearingEnabled: true },
+    });
+    if (bookings.length === 0) return;
+
+    const milestoneRepo = this.dataSource.getRepository(ClearanceMilestone);
+    const rows = await milestoneRepo.find({
+      where: {
+        bookingId: In(bookings.map((b) => b.id)),
+        milestoneCode: 'GATEPASS_GRANTED',
+      },
+    });
+
+    for (const row of rows) {
+      if (row.status === 'COMPLETED') continue;
+      row.status = 'COMPLETED';
+      row.triggeredAt = securedAt;
+      row.metadata = { ...(row.metadata ?? {}), gatepassAt: securedAt.toISOString() };
+      await milestoneRepo.save(row);
+    }
+  }
+
   async markImportReadyForLoading(scheduleId: string, dto: ImportDjiboutiActionDto = {}) {
     const schedule = await this.getImportDjiboutiSchedule(scheduleId);
     const operation = await this.getOrCreateImportDjiboutiOperation(scheduleId);