diff --git a/apps/edr-freight-api/src/modules/billing/billing.service.spec.ts b/apps/edr-freight-api/src/modules/billing/billing.service.spec.ts
index 037957367..e7682879b 100644
--- a/apps/edr-freight-api/src/modules/billing/billing.service.spec.ts
+++ b/apps/edr-freight-api/src/modules/billing/billing.service.spec.ts
@@ -376,4 +376,97 @@ describe("BillingService.expirePayable — locked write runs in a transaction",
     expect(result).toBeNull();
     expect(transaction).not.toHaveBeenCalled();
   });
+
+  it("also retires a DRAFT invoice — a superseded/cancelled source must not leave one behind", async () => {
+    const { service, defaultManager } = build({
+      ...openInvoice,
+      status: Freight.InvoiceStatus.Draft,
+    });
+
+    await service.expirePayable(
+      Freight.InvoiceSource.Booking,
+      "booking-1",
+      "prepaid",
+    );
+
+    const { where } = defaultManager.findOne.mock.calls[0][1];
+    expect(where.status.value).toContain(Freight.InvoiceStatus.Draft);
+  });
+});
+
+describe("BillingService.issuePayable", () => {
+  const dueAt = new Date("2026-01-02T00:00:00.000Z");
+
+  const build = (found: Record<string, unknown> | null) => {
+    const manager = {
+      findOne: jest.fn().mockResolvedValue(found),
+      update: jest.fn().mockResolvedValue(undefined),
+    };
+    const service = new BillingService(
+      { manager, transaction: jest.fn() } as never,
+      {} as never,
+      {} as never,
+      makeEvents() as never,
+      {} as never,
+      {} as never,
+      {} as never,
+    );
+    return { service, manager };
+  };
+
+  const issue = (service: BillingService) =>
+    service.issuePayable(
+      Freight.InvoiceSource.Booking,
+      "booking-1",
+      dueAt,
+      "PREPAID",
+    );
+
+  it("issues a DRAFT invoice to PENDING, stamping issuedAt and the pay-window dueAt", async () => {
+    const { service, manager } = build({
+      id: "inv-1",
+      invoiceNumber: "INV-20260101-00001",
+      status: Freight.InvoiceStatus.Draft,
+      issuedAt: null,
+    });
+
+    const result = await issue(service);
+
+    const patch = manager.update.mock.calls[0][2];
+    expect(patch.status).toBe(Freight.InvoiceStatus.Pending);
+    expect(patch.dueAt).toBe(dueAt);
+    expect(patch.issuedAt).toBeInstanceOf(Date);
+    expect(result?.status).toBe(Freight.InvoiceStatus.Pending);
+  });
+
+  it("looks up DRAFT invoices — a booking's invoice is minted DRAFT and this is what makes it payable", async () => {
+    const { service, manager } = build(null);
+
+    await issue(service);
+
+    const { where } = manager.findOne.mock.calls[0][1];
+    expect(where.status.value).toContain(Freight.InvoiceStatus.Draft);
+  });
+
+  it("only refreshes dueAt on an already-issued invoice, so a re-reserve never re-issues", async () => {
+    const issuedAt = new Date("2026-01-01T00:00:00.000Z");
+    const { service, manager } = build({
+      id: "inv-1",
+      invoiceNumber: "INV-20260101-00001",
+      status: Freight.InvoiceStatus.Pending,
+      issuedAt,
+    });
+
+    const result = await issue(service);
+
+    expect(manager.update.mock.calls[0][2]).toEqual({ dueAt });
+    expect(result?.issuedAt).toBe(issuedAt);
+  });
+
+  it("is a no-op (returns null, writes nothing) when the source has no draft-or-open invoice", async () => {
+    const { service, manager } = build(null);
+
+    await expect(issue(service)).resolves.toBeNull();
+    expect(manager.update).not.toHaveBeenCalled();
+  });
 });
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 3b14d6f4c..4d647e3ef 100644
--- a/apps/edr-freight-api/src/modules/billing/billing.service.ts
+++ b/apps/edr-freight-api/src/modules/billing/billing.service.ts
@@ -826,8 +826,15 @@ export class BillingService {
    * Expire a source's currently-open invoice (its pay window closed before
    * settlement), then emit `${source}.invoice.expired`. Resolves the open invoice
    * and transitions it to EXPIRED — a terminal, non-payable status (kept out of
-   * `OPEN_STATUSES`). No-op (returns null) when the source has no open invoice
-   * (already paid/cancelled/expired).
+   * `OPEN_STATUSES`). No-op (returns null) when the source has no invoice left to
+   * retire (already paid/cancelled/expired).
+   *
+   * DRAFT invoices are matched too, even though they were never issued: this is
+   * also the "retire the invoice this source no longer needs" path (a cancelled
+   * booking, or a full-amount invoice superseded by a partial-offer one). Skipping
+   * drafts would leave the stale one behind for `findPayable` to hand back — the
+   * superseding invoice would then never be minted, and a cancelled booking would
+   * keep a draft that a later `issuePayable` could still make payable.
    *
    * Pass the caller's transaction `manager` (e.g. the booking pay-window expiry in
    * the batch engine) to enlist in its DB transaction.
@@ -850,7 +857,7 @@ export class BillingService {
       where: {
         source,
         sourceId,
-        status: In(OPEN_STATUSES),
+        status: In([Freight.InvoiceStatus.Draft, ...OPEN_STATUSES]),
         ...(type ? { type } : {}),
       },
       order: { issuedAt: "DESC" },
@@ -867,30 +874,58 @@ export class BillingService {
   }
 
   /**
-   * Sync a source's open invoice `dueAt` to its real pay-window deadline. The
-   * booking invoice is generated before the pay window opens (at booking
-   * creation/approval), so its printed due date is refreshed when the batch engine
-   * sets `paymentDeadline`. No-op when the source has no open invoice.
+   * Issue a source's invoice and stamp its real pay-window deadline — the single
+   * transition that makes a source payable.
+   *
+   * A source's invoice is minted DRAFT, before any pay window exists (e.g. a
+   * booking invoice is generated at creation / operation-accept, long before the
+   * batch engine reserves a slot). DRAFT is deliberately outside `OPEN_STATUSES`,
+   * so such an invoice is not settleable and the portal renders no pay button.
+   * The domain calls this at the moment the pay window actually opens (booking →
+   * `reserve`, which sets SELECTED_FOR_BATCH + `paymentDeadline`), which issues
+   * the draft (→ PENDING, stamping `issuedAt`) and prints the real `dueAt`.
+   *
+   * Idempotent: an already-issued open invoice only has its `dueAt` refreshed, so
+   * a re-reserve never re-issues. No-op (returns null) when the source has no
+   * draft-or-open invoice (already paid/cancelled/expired).
    */
-  async syncPayableDueDate(
+  async issuePayable(
     source: Freight.InvoiceSource,
     sourceId: string,
     dueAt: Date,
     type?: string,
     manager?: EntityManager,
-  ): Promise<void> {
+  ): Promise<Invoice | null> {
     const mg = manager ?? this.dataSource.manager;
     const invoice = await mg.findOne(Invoice, {
       where: {
         source,
         sourceId,
-        status: In(OPEN_STATUSES),
+        status: In([Freight.InvoiceStatus.Draft, ...OPEN_STATUSES]),
         ...(type ? { type } : {}),
       },
       order: { issuedAt: "DESC" },
     });
-    if (!invoice) return;
-    await mg.update(Invoice, { id: invoice.id }, { dueAt });
+    if (!invoice) return null;
+
+    const issuing = invoice.status === Freight.InvoiceStatus.Draft;
+    const patch = {
+      dueAt,
+      ...(issuing
+        ? {
+            status: Freight.InvoiceStatus.Pending,
+            issuedAt: invoice.issuedAt ?? new Date(),
+          }
+        : {}),
+    };
+    await mg.update(Invoice, { id: invoice.id }, patch);
+
+    if (issuing) {
+      this.logger.log(
+        `Issued invoice ${invoice.invoiceNumber} (${invoice.id}) for ${source}:${sourceId} — payable until ${dueAt.toISOString()}`,
+      );
+    }
+    return { ...invoice, ...patch } as Invoice;
   }
 
   /**
diff --git a/apps/edr-freight-api/src/modules/bookings/booking-transition.service.ts b/apps/edr-freight-api/src/modules/bookings/booking-transition.service.ts
index 69d505c3b..2aed86027 100644
--- a/apps/edr-freight-api/src/modules/bookings/booking-transition.service.ts
+++ b/apps/edr-freight-api/src/modules/bookings/booking-transition.service.ts
@@ -33,8 +33,6 @@ import { ClearanceMilestoneService } from '../contracts/clearance-milestone.serv
 import { ClearanceWorkflowService } from '../contracts/clearance-workflow.service';
 import { ContractDocPhase } from '@edr/types';
 
-
-import { Freight } from "@edr/types";
 import { BookingInvoiceService } from "./booking-invoice.service";
 
 @Injectable()
@@ -1112,14 +1110,25 @@ export class BookingTransitionService {
       await this.bookingBatchService.pickExportSchedule(booking);
     }
 
+    // Mint the booking's invoice (DRAFT) so the priced order carries its billing
+    // record from accept onward. It is deliberately NOT issued here: accepting an
+    // operation only puts the booking in the batch holding pool — no slot has been
+    // offered and no pay window exists yet. Issuing at this point made the invoice
+    // payable straight away (portal invoice list/detail gate on invoice status
+    // alone), letting a customer pay before being selected for a batch, while the
+    // booking page correctly still showed it as not payable. The batch engine
+    // issues it in `reserve` (SELECTED_FOR_BATCH), which is where the pay window
+    // and the real deadline are created — matching the portal's `canPay` gate.
     const invoice = await this.invoiceService.ensureInvoiceForBooking(booking);
     this.logger.log(
-      `Generated invoice ${invoice.invoiceNumber} (${invoice.id}) for ${booking.reference}:${booking.id}`,
-    );
-    await this.invoiceService.updateStatus(
-      invoice.id,
-      Freight.InvoiceStatus.Pending,
+      `Generated draft invoice ${invoice.invoiceNumber} (${invoice.id}) for ${booking.reference}:${booking.id} — issued on batch selection`,
     );
+    // TODO: road (truck) orders are an incomplete feature — they stop at the
+    // dead-end ROAD_DISPATCH_PENDING status below (no dispatch transition, no
+    // per-km pricing wired via roadKmPrice, no pay surface in the portal). They
+    // skip the train batch, so they never reach `reserve` and their invoice stays
+    // DRAFT / unpayable. When the road flow is built, issue its invoice
+    // (billing.issuePayable) at whatever transition opens the road pay window.
     if (isRoadService(booking.serviceType)) {
       await this.bookingsRepository.update(booking.id, {
         status: "ROAD_DISPATCH_PENDING",
diff --git a/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.spec.ts b/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.spec.ts
index c37430121..8c3c92193 100644
--- a/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.spec.ts
+++ b/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.spec.ts
@@ -134,7 +134,7 @@ describe('BookingBatchService — PAID reconcile', () => {
       { addTimeout: jest.fn(), deleteTimeout: jest.fn(), doesExist: jest.fn() } as never,
       trainSchedulingService as never,
       {
-        syncPayableDueDate: jest.fn().mockResolvedValue(undefined),
+        issuePayable: jest.fn().mockResolvedValue(null),
         expirePayable: jest.fn().mockResolvedValue(undefined),
       } as never,
       { emitPhase: jest.fn() } as never,
@@ -596,7 +596,7 @@ describe('BookingBatchService — PAID reconcile', () => {
         notifier as never,
         { addTimeout: jest.fn(), deleteTimeout: jest.fn(), doesExist: jest.fn() } as never,
         trainSchedulingService as never,
-        { syncPayableDueDate: jest.fn(), expirePayable: jest.fn() } as never,
+        { issuePayable: jest.fn(), expirePayable: jest.fn() } as never,
         { emitPhase: jest.fn() } as never,
         { computeSubmitPriorityScore: jest.fn().mockResolvedValue(0) } as never,
         undefined,
@@ -619,7 +619,7 @@ describe('BookingBatchService — PAID reconcile', () => {
         notifier as never,
         { addTimeout: jest.fn(), deleteTimeout: jest.fn(), doesExist: jest.fn() } as never,
         trainSchedulingService as never,
-        { syncPayableDueDate: jest.fn(), expirePayable: jest.fn() } as never,
+        { issuePayable: jest.fn(), expirePayable: jest.fn() } as never,
         { emitPhase: jest.fn() } as never,
         { computeSubmitPriorityScore: jest.fn().mockResolvedValue(0) } as never,
         undefined,
@@ -650,7 +650,7 @@ describe('BookingBatchService — PAID reconcile', () => {
         notifier as never,
         { addTimeout: jest.fn(), deleteTimeout: jest.fn(), doesExist: jest.fn() } as never,
         trainSchedulingService as never,
-        { syncPayableDueDate: jest.fn(), expirePayable: jest.fn() } as never,
+        { issuePayable: jest.fn(), expirePayable: jest.fn() } as never,
         { emitPhase: jest.fn() } as never,
         { computeSubmitPriorityScore: jest.fn().mockResolvedValue(0) } as never,
         undefined,
diff --git a/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.ts b/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.ts
index 18e1c0fc7..ef39ab138 100644
--- a/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.ts
+++ b/apps/edr-freight-api/src/modules/train-scheduling/booking-batch.service.ts
@@ -2317,9 +2317,13 @@ export class BookingBatchService implements OnModuleInit {
       paymentDeadline: deadline,
     } as never);
     booking.trainScheduleId = scheduleId;
-    // The invoice was generated at booking creation/approval, before this pay
-    // window opened — refresh its printed due date to the real deadline.
-    await this.billing.syncPayableDueDate(
+    // The invoice was generated DRAFT at booking creation / operation-accept,
+    // before this pay window existed. Reserving is the moment the booking becomes
+    // payable (SELECTED_FOR_BATCH + a real deadline), so issue the draft here and
+    // print the deadline as its due date — never earlier, or the customer could
+    // settle an invoice for a slot they have not been offered yet. Idempotent: a
+    // re-reserve only refreshes `dueAt`.
+    await this.billing.issuePayable(
       Freight.InvoiceSource.Booking,
       booking.id,
       deadline,