diff --git a/apps/edr-freight-web/portal/src/pages/bookings/NewBookingPage.tsx b/apps/edr-freight-web/portal/src/pages/bookings/NewBookingPage.tsx
index 52cbb46f8..5ada990d1 100644
--- a/apps/edr-freight-web/portal/src/pages/bookings/NewBookingPage.tsx
+++ b/apps/edr-freight-web/portal/src/pages/bookings/NewBookingPage.tsx
@@ -22,6 +22,7 @@ import {
   Step2ServiceType,
   Step4Route,
   Step5CargoDetails,
+  StepDocuments,
   Step8Review,
 } from "./new-booking-form/steps";
 
@@ -34,8 +35,25 @@ export default function NewBookingPage() {
   );
 
   const createMutation = useMutation({
-    mutationFn: (payload: CreateBookingPayload) =>
-      api.bookings.create.call(payload),
+    mutationFn: async (payload: CreateBookingPayload) => {
+      const booking = await api.bookings.create.call(payload);
+
+      // Documents can't ride along with creation — upload them against the
+      // new booking id once it exists. Optional here; the booking detail page
+      // remains the catch-all for any docs the user skips.
+      const documents = form.getValues("documents") ?? {};
+      const hasDocuments = Object.values(documents).some((value) =>
+        Array.isArray(value) ? value.length > 0 : Boolean(value),
+      );
+      if (hasDocuments) {
+        await api.bookings.uploadDocuments.call({
+          id: booking.id,
+          files: documents,
+        });
+      }
+
+      return booking;
+    },
     onSuccess: (booking) => {
       queryClient.invalidateQueries({ queryKey: api.bookings.list.queryKey() });
       navigate(`/bookings/${booking.id}`);
@@ -282,7 +300,8 @@ export default function NewBookingPage() {
                 isLoading={refDataLoading}
               />
             )}
-            {step === 5 && (
+            {step === 5 && <StepDocuments form={form} />}
+            {step === 6 && (
               <Step8Review
                 form={form}
                 setStep={setStep}
diff --git a/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/schema.ts b/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/schema.ts
index be443d081..86d3571ec 100644
--- a/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/schema.ts
+++ b/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/schema.ts
@@ -1,3 +1,4 @@
+import type { Freight } from "@edr/types";
 import { DeepPartial, Path } from "react-hook-form";
 import * as z from "zod";
 
@@ -22,9 +23,61 @@ export const STEPS = [
   { id: 2, label: "Service Type & Mile", short: "Service" },
   { id: 3, label: "Route", short: "Route" },
   { id: 4, label: "Cargo Details", short: "Cargo" },
-  { id: 5, label: "Review & Submit", short: "Submit" },
+  { id: 5, label: "Documents", short: "Documents" },
+  { id: 6, label: "Review & Submit", short: "Submit" },
 ] as const;
 
+/**
+ * Shipment documents collected during booking creation. The fileKeys mirror
+ * `REQUIRED_DOC_FIELDS` in BookingDetailPage/constants.ts so anything attached
+ * here shows up as "Uploaded" on the booking detail page. All optional in this
+ * flow — the detail page remains the catch-all for uploading them later.
+ */
+const DOC_SETTING_TS = "2024-01-01T00:00:00.000Z";
+
+function docField(
+  fileKey: string,
+  fileLabel: string,
+  order: number,
+): Freight.IFileUploadField {
+  return {
+    id: fileKey,
+    settingId: "booking_documents",
+    createdAt: DOC_SETTING_TS,
+    updatedAt: DOC_SETTING_TS,
+    deletedAt: null,
+    fileKey,
+    fileLabel,
+    helpText: null,
+    isRequired: false,
+    isMultiple: false,
+    maxFiles: 1,
+    allowedExtensions: ["pdf", "jpg", "jpeg", "png"],
+    maxSizeMb: 10,
+    order,
+  };
+}
+
+export const BOOKING_DOCS_SETTING: Freight.IFileUploadSetting = {
+  id: "booking_documents",
+  createdAt: DOC_SETTING_TS,
+  updatedAt: DOC_SETTING_TS,
+  deletedAt: null,
+  code: "booking_documents",
+  label: "Booking Documents",
+  description:
+    "Attach your shipment documents now, or skip and upload them later from the booking page.",
+  entity: "booking",
+  fields: [
+    docField("commercial_invoice", "Commercial Invoice", 1),
+    docField("packing_list", "Packing List", 2),
+    docField("certificate_of_origin", "Certificate of Origin", 3),
+    docField("letter_of_credit", "Letter of Credit / LC", 4),
+  ],
+};
+
+export type BookingDocuments = Record<string, File | File[] | null>;
+
 export const bookingFormSchema = z
   .object({
     contractType: z.enum(["new", "renewal"], "Select a contract type."),
@@ -78,6 +131,7 @@ export const bookingFormSchema = z
       }),
     ),
     consolidationEnabled: z.boolean(),
+    documents: z.record(z.string(), z.any()).default({}),
     notes: z.string(),
     termsAccepted: z.boolean(),
   })
@@ -187,6 +241,7 @@ export const initialBookingFormValues: DeepPartial<BookingFormValues> = {
   isRefrigerated: false,
   containers: [{ type: "20ft", containerType: "", qty: "1", vgm: "" }],
   consolidationEnabled: false,
+  documents: {},
   notes: "",
   termsAccepted: false,
 };
@@ -215,7 +270,8 @@ export const stepFields: Record<number, Array<Path<BookingFormValues>>> = {
     "containers",
     "consolidationEnabled",
   ],
-  5: ["notes", "termsAccepted"],
+  5: ["documents"],
+  6: ["notes", "termsAccepted"],
 };
 
 export type RouteDirection = "import" | "export" | "domestic" | null;
diff --git a/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/step-documents.tsx b/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/step-documents.tsx
new file mode 100644
index 000000000..cd7db7b85
--- /dev/null
+++ b/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/step-documents.tsx
@@ -0,0 +1,82 @@
+import { Box, Group, Text } from "@mantine/core";
+import { SmartFileInput } from "@edr/ui-common";
+import { CheckCircle2 } from "lucide-react";
+import { Controller, type UseFormReturn } from "react-hook-form";
+
+import {
+  BOOKING_DOCS_SETTING,
+  type BookingDocuments,
+  type BookingFormValues,
+} from "./schema";
+import { StepHeader } from "./shared";
+
+type BookingForm = UseFormReturn<BookingFormValues>;
+
+function countAttached(documents: BookingDocuments): number {
+  return BOOKING_DOCS_SETTING.fields.filter((f) => {
+    const value = documents[f.fileKey];
+    return Array.isArray(value) ? value.length > 0 : Boolean(value);
+  }).length;
+}
+
+export function StepDocuments({ form }: { form: BookingForm }) {
+  const documents = (form.watch("documents") ?? {}) as BookingDocuments;
+  const attached = countAttached(documents);
+  const total = BOOKING_DOCS_SETTING.fields.length;
+
+  return (
+    <div className="space-y-6">
+      <StepHeader
+        title="Shipment Documents"
+        description="Attach your shipment documents now, or skip this step and upload them later from the booking page."
+      />
+
+      <Group
+        gap={10}
+        align="center"
+        wrap="nowrap"
+        className="rounded-xl"
+        style={{
+          border: "1px solid var(--mantine-color-edr-border-0)",
+          backgroundColor: "var(--mantine-color-gray-0)",
+          padding: "12px 16px",
+        }}
+      >
+        <Box
+          style={{
+            flexShrink: 0,
+            width: 32,
+            height: 32,
+            display: "flex",
+            alignItems: "center",
+            justifyContent: "center",
+            borderRadius: 999,
+            fontSize: 12,
+            fontWeight: 700,
+            backgroundColor: attached === total ? "#ECF6F1" : "#EAF1FB",
+            color: attached === total ? "#0A6F4D" : "#2E5B96",
+          }}
+        >
+          {attached === total ? <CheckCircle2 size={16} /> : `${attached}/${total}`}
+        </Box>
+        <Text size="sm" c="dimmed">
+          {attached === 0
+            ? "All documents are optional here — you can upload them later from the booking page."
+            : `${attached} of ${total} attached. You can finish the rest later from the booking page.`}
+        </Text>
+      </Group>
+
+      <Controller
+        name="documents"
+        control={form.control}
+        render={({ field }) => (
+          <SmartFileInput
+            file={BOOKING_DOCS_SETTING}
+            value={(field.value ?? {}) as BookingDocuments}
+            onChange={(value) => field.onChange(value)}
+          />
+        )}
+      />
+    </div>
+  );
+}
diff --git a/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/steps.tsx b/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/steps.tsx
index 7e47282aa..9f1445f91 100644
--- a/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/steps.tsx
+++ b/apps/edr-freight-web/portal/src/pages/bookings/new-booking-form/steps.tsx
@@ -2,4 +2,5 @@ export { Step1ContractType } from "./step1-contract-type";
 export { Step2ServiceType } from "./step2-service-type";
 export { Step4Route } from "./step4-route";
 export { Step5CargoDetails } from "./step5-cargo-details";
+export { StepDocuments } from "./step-documents";
 export { Step8Review } from "./step8-review";