diff --git a/apps/edr-freight-web/portal/src/pages/MyPortalPage/MyPortalPage.tsx b/apps/edr-freight-web/portal/src/pages/MyPortalPage/MyPortalPage.tsx
index 98ed091f9..cb350916d 100644
--- a/apps/edr-freight-web/portal/src/pages/MyPortalPage/MyPortalPage.tsx
+++ b/apps/edr-freight-web/portal/src/pages/MyPortalPage/MyPortalPage.tsx
@@ -96,6 +96,7 @@ export default function MyPortalPage() {
         <Grid.Col span={{ base: 12, lg: 6 }}>
           <RecentContractsSection
             contracts={recentContracts}
+            bookings={allBookings}
             isLoading={contractsQuery.isPending}
           />
         </Grid.Col>
diff --git a/apps/edr-freight-web/portal/src/pages/MyPortalPage/components/RecentContractsSection.tsx b/apps/edr-freight-web/portal/src/pages/MyPortalPage/components/RecentContractsSection.tsx
index 898173942..14ac28b2b 100644
--- a/apps/edr-freight-web/portal/src/pages/MyPortalPage/components/RecentContractsSection.tsx
+++ b/apps/edr-freight-web/portal/src/pages/MyPortalPage/components/RecentContractsSection.tsx
@@ -1,12 +1,13 @@
 import { Box, Button, Group, Skeleton, Stack, Text } from "@mantine/core";
 import { memo } from "react";
 import { useNavigate } from "react-router-dom";
-import { ArrowRight, FileSignature, Package, Plus } from "lucide-react";
+import { ArrowRight, FileSignature, Package, Plus, RefreshCw } from "lucide-react";
 import type { Freight } from "@edr/types";
 import {
   ContractDocButton,
   ContractStatusBadge,
 } from "@/pages/contracts/contract-ui";
+import { getContractBookingAction } from "@/pages/contracts/contract-booking-action";
 import { Card } from "./Card";
 import { EmptyState } from "./EmptyState";
 
@@ -14,16 +15,15 @@ const INK = "#10202F";
 const MUTED = "#6B7C8E";
 const BORDER = "#E6ECF2";
 
-// Statuses where a Path A customer may book directly against the contract.
-const BOOKABLE = ["FULLY_EXECUTED", "CONTRACT_ACTIVE"];
-
 interface RecentContractsSectionProps {
   contracts: Freight.IContract[];
+  bookings: Freight.IBooking[];
   isLoading: boolean;
 }
 
 export const RecentContractsSection = memo(function RecentContractsSection({
   contracts,
+  bookings,
   isLoading,
 }: RecentContractsSectionProps) {
   const navigate = useNavigate();
@@ -65,7 +65,7 @@ export const RecentContractsSection = memo(function RecentContractsSection({
             const isGeneral = c.contractKind === "GENERAL";
             const isContainer = c.freightType === "CONTAINER";
             const canSign = c.status === "CONTRACT_READY";
-            const canBook = !c.customsClearingEnabled && BOOKABLE.includes(c.status);
+            const bookingAction = getContractBookingAction(c, bookings);
             return (
               <Group
                 key={c.id}
@@ -109,18 +109,24 @@ export const RecentContractsSection = memo(function RecentContractsSection({
                     >
                       Sign
                     </Button>
-                  ) : canBook ? (
+                  ) : bookingAction.kind !== "none" ? (
                     <Button
                       size="xs"
                       radius="md"
                       color="edr-green"
-                      leftSection={<Package size={13} />}
+                      leftSection={
+                        bookingAction.kind === "rebook" ? (
+                          <RefreshCw size={13} />
+                        ) : (
+                          <Package size={13} />
+                        )
+                      }
                       onClick={(e) => {
                         e.stopPropagation();
-                        navigate(`/contracts/${c.id}/bookings/new`);
+                        navigate(bookingAction.to);
                       }}
                     >
-                      Book
+                      {bookingAction.kind === "rebook" ? "Re-book" : "Book"}
                     </Button>
                   ) : (
                     <Button
diff --git a/apps/edr-freight-web/portal/src/pages/bookings/BookingDetailPage/ReadonlyBookingView.tsx b/apps/edr-freight-web/portal/src/pages/bookings/BookingDetailPage/ReadonlyBookingView.tsx
index 73bb61129..b5b29e79c 100644
--- a/apps/edr-freight-web/portal/src/pages/bookings/BookingDetailPage/ReadonlyBookingView.tsx
+++ b/apps/edr-freight-web/portal/src/pages/bookings/BookingDetailPage/ReadonlyBookingView.tsx
@@ -40,6 +40,13 @@ export function ReadonlyBookingView({ booking }: { booking: Freight.IBooking })
   const [payModalOpen, setPayModalOpen] = useState(false);
   const { view, viewer } = useFileViewer();
 
+  // Re-book opens the New Shipment Booking form for the same contract, not the
+  // New Contract page. Fall back to /contracts/new only if the link is missing.
+  const rebookTo = booking.contractId
+    ? `/contracts/${booking.contractId}/bookings/new`
+    : "/contracts/new";
+  const onRebook = () => navigate(rebookTo);
+
   // POST /payments/initiate creates the intent and returns the provider's
   // redirect URL (clientAction.url). Send the browser straight there; fall back
   // to the public /payments/checkout page if no redirect URL came back.
@@ -98,7 +105,7 @@ export function ReadonlyBookingView({ booking }: { booking: Freight.IBooking })
         }
         menuActions={{
           onViewContract: booking.signedByCeoAt ? () => {} : undefined,
-          onRebook: () => navigate("/bookings/new", { state: { fresh: true } }),
+          onRebook,
           onSupport: () => navigate("/support"),
         }}
       />
@@ -115,14 +122,14 @@ export function ReadonlyBookingView({ booking }: { booking: Freight.IBooking })
               : "This booking process has been terminated."
           }
           reason={booking.latestChangeRequestNote}
-          onRebook={() => navigate("/bookings/new", { state: { fresh: true } })}
+          onRebook={onRebook}
         />
       ) : isExpired ? (
         <CancelledBanner
           pillLabel="Expired"
           title={`The payment window expired on ${fmtDate(booking.updatedAt)}.`}
           subtitle="Payment wasn't completed in time, so this booking lost its slot. Rebook to try another schedule."
-          onRebook={() => navigate("/bookings/new", { state: { fresh: true } })}
+          onRebook={onRebook}
         />
       ) : isPendingConsolidation ? (
         <ConsolidationWaitingBanner
diff --git a/apps/edr-freight-web/portal/src/pages/contracts/ContractsList.tsx b/apps/edr-freight-web/portal/src/pages/contracts/ContractsList.tsx
index dcd370a6f..e53b5869a 100644
--- a/apps/edr-freight-web/portal/src/pages/contracts/ContractsList.tsx
+++ b/apps/edr-freight-web/portal/src/pages/contracts/ContractsList.tsx
@@ -32,6 +32,7 @@ import {
 import { api } from "@/services/api";
 import type { ContractListFilter } from "@/services/contracts.service";
 import type { Freight } from "@edr/types";
+import { getContractBookingAction } from "./contract-booking-action";
 import { usePagination } from "@edr/ui-common";
 import {
   BORDER,
@@ -52,7 +53,6 @@ function primaryRoute(contract: Freight.IContract) {
   };
 }
 
-const PATH_A_BOOKABLE_STATUSES = ["FULLY_EXECUTED", "CONTRACT_ACTIVE"];
 const PATH_B_CLEARANCE_STATUSES = [
   "AWAITING_CLEARANCE_DOCUMENTS",
   "CLEARANCE_UNDER_REVIEW",
@@ -62,6 +62,7 @@ const PATH_B_CLEARANCE_STATUSES = [
 /** The single most relevant next action for a customer's contract row. */
 function getCustomerRowAction(
   contract: Freight.IContract,
+  bookings: Freight.IBooking[],
 ): { label: string; to: string; primary: boolean } {
   const id = contract.id;
   if (contract.status === "CONTRACT_READY") {
@@ -80,15 +81,12 @@ function getCustomerRowAction(
       primary: true,
     };
   }
-  if (
-    !contract.customsClearingEnabled &&
-    PATH_A_BOOKABLE_STATUSES.includes(contract.status)
-  ) {
-    return {
-      label: "Book shipment",
-      to: `/contracts/${id}/bookings/new`,
-      primary: true,
-    };
+  const booking = getContractBookingAction(contract, bookings);
+  if (booking.kind === "book") {
+    return { label: "Book shipment", to: booking.to, primary: true };
+  }
+  if (booking.kind === "rebook") {
+    return { label: "Re-book shipment", to: booking.to, primary: true };
   }
   return { label: "View", to: `/contracts/${id}`, primary: false };
 }
@@ -139,6 +137,15 @@ export default function ContractsList() {
     api.contracts.list.queryOptions({ input: filter }),
   );
 
+  // Bookings have no embedded link on the contract list, so cross-reference
+  // them to decide Book / Re-book per row (see getContractBookingAction).
+  const { data: bookingsData } = useQuery(
+    api.bookings.list.queryOptions({
+      input: { sortBy: "createdAt", sortOrder: "DESC" },
+    }),
+  );
+  const bookings = bookingsData?.items ?? [];
+
   const rows = useMemo(() => {
     const items = data?.items ?? [];
     if (!query.trim()) return items;
@@ -407,7 +414,7 @@ export default function ContractsList() {
                     const tradeLabel = dir
                       ? dir.charAt(0) + dir.slice(1).toLowerCase()
                       : "—";
-                    const action = getCustomerRowAction(c);
+                    const action = getCustomerRowAction(c, bookings);
                     return (
                       <Table.Tr
                         key={c.id}
diff --git a/apps/edr-freight-web/portal/src/pages/contracts/contract-booking-action.ts b/apps/edr-freight-web/portal/src/pages/contracts/contract-booking-action.ts
new file mode 100644
index 000000000..0264ce064
--- /dev/null
+++ b/apps/edr-freight-web/portal/src/pages/contracts/contract-booking-action.ts
@@ -0,0 +1,54 @@
+import type { Freight } from "@edr/types";
+
+/**
+ * Booking statuses that no longer occupy the single active-booking slot of a
+ * ONE_TIME contract. Mirrors the API source of truth in
+ * `contract-booking.service.ts`.
+ */
+export const TERMINAL_BOOKING_STATUSES = [
+  "EXPIRED",
+  "CANCELLED",
+  "COMPLETED",
+  "REJECTED",
+];
+
+/** Path A statuses where a customer (no customs) may book against the contract. */
+const PATH_A_BOOKABLE = ["FULLY_EXECUTED", "CONTRACT_ACTIVE"];
+
+export type ContractBookingActionKind = "book" | "rebook" | "none";
+
+export interface ContractBookingAction {
+  kind: ContractBookingActionKind;
+  to: string;
+}
+
+/**
+ * The single source of truth for whether a contract row should show a
+ * Book / Re-book shipment button, and where it should navigate.
+ *
+ * - ONE_TIME: book only while there is no active booking. If the previous
+ *   booking expired, offer Re-book. Once a live booking exists, no button.
+ * - GENERAL: bookable while CONTRACT_ACTIVE (CONTRACT_CLOSED / EXPIRED are
+ *   already excluded by the PATH_A_BOOKABLE gate).
+ */
+export function getContractBookingAction(
+  contract: Freight.IContract,
+  bookings: Freight.IBooking[],
+): ContractBookingAction {
+  if (contract.customsClearingEnabled) return { kind: "none", to: "" };
+  if (!PATH_A_BOOKABLE.includes(contract.status)) return { kind: "none", to: "" };
+
+  const to = `/contracts/${contract.id}/bookings/new`;
+
+  if (contract.contractKind === "ONE_TIME") {
+    const mine = bookings.filter((b) => b.contractId === contract.id);
+    const hasActive = mine.some(
+      (b) => !TERMINAL_BOOKING_STATUSES.includes(b.status),
+    );
+    if (hasActive) return { kind: "none", to: "" };
+    const hasExpired = mine.some((b) => b.status === "EXPIRED");
+    return { kind: hasExpired ? "rebook" : "book", to };
+  }
+
+  return { kind: "book", to };
+}
diff --git a/packages/types/src/freight/index.ts b/packages/types/src/freight/index.ts
index 943d1e17c..b3d58288b 100644
--- a/packages/types/src/freight/index.ts
+++ b/packages/types/src/freight/index.ts
@@ -354,6 +354,8 @@ export interface IYard extends BaseEntity {
 export interface IBooking extends BaseEntity {
   reference: string;
   customerId: string;
+  /** The contract this booking was created under (Path A / Path B). */
+  contractId?: string | null;
   trainId?: string | null;
   status: BookingStatus;
   /** ONE_TIME for normal bookings; GENERAL_CONTRACT for umbrella contracts. */