diff --git a/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-detail.png b/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-detail.png
index 3a0601f5..233cd701 100644
Binary files a/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-detail.png and b/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-detail.png differ
diff --git a/src/app/(protected)/workorders/_components/uplifts/uplift-attachment-picker.tsx b/src/app/(protected)/workorders/_components/uplifts/uplift-attachment-picker.tsx
index 48bfe671..bb8d8d57 100644
--- a/src/app/(protected)/workorders/_components/uplifts/uplift-attachment-picker.tsx
+++ b/src/app/(protected)/workorders/_components/uplifts/uplift-attachment-picker.tsx
@@ -6,8 +6,8 @@ import { Text } from "@/components/ui/text";
 const ACCEPTED_TYPES = new Set(["application/pdf", "image/jpeg", "image/jpg", "image/png"]);
 
 type UpliftAttachmentPickerProps = {
-  file: File | null;
-  onChange: (file: File | null) => void;
+  files: File[];
+  onChange: (files: File[]) => void;
 };
 
 function isAllowedUpliftEvidenceFile(file: File): boolean {
@@ -15,9 +15,9 @@ function isAllowedUpliftEvidenceFile(file: File): boolean {
   return /\.(pdf|jpe?g|png)$/i.test(file.name);
 }
 
-function firstAllowedFile(incoming: FileList | null): File | null {
-  if (!incoming || incoming.length === 0) return null;
-  return Array.from(incoming).find(isAllowedUpliftEvidenceFile) ?? null;
+function allowedFiles(incoming: FileList | null): File[] {
+  if (!incoming || incoming.length === 0) return [];
+  return Array.from(incoming).filter(isAllowedUpliftEvidenceFile);
 }
 
 function UpliftStagedFile({ file, onRemove }: { file: File; onRemove: () => void }) {
@@ -46,19 +46,20 @@ function UpliftStagedFile({ file, onRemove }: { file: File; onRemove: () => void
   );
 }
 
-export function UpliftAttachmentPicker({ file, onChange }: UpliftAttachmentPickerProps) {
+export function UpliftAttachmentPicker({ files, onChange }: UpliftAttachmentPickerProps) {
   const inputRef = useRef<HTMLInputElement>(null);
 
-  const stageFile = (incoming: FileList | null) => {
-    const next = firstAllowedFile(incoming);
-    if (next) onChange(next);
+  const stageFiles = (incoming: FileList | null) => {
+    const next = allowedFiles(incoming);
+    if (next.length === 0) return;
+    onChange([...files, ...next]);
   };
 
   return (
     <div className="mt-4">
       <FieldLabel>Attachment</FieldLabel>
       <Text as="p" variant="caption" tone="muted" className="mb-2">
-        Optional — PDF, JPG, or PNG.
+        Optional — one or more PDF, JPG, or PNG files.
       </Text>
       <button
         type="button"
@@ -66,7 +67,7 @@ export function UpliftAttachmentPicker({ file, onChange }: UpliftAttachmentPicke
         onDragOver={(event) => event.preventDefault()}
         onDrop={(event) => {
           event.preventDefault();
-          stageFile(event.dataTransfer.files);
+          stageFiles(event.dataTransfer.files);
         }}
         className="flex w-full items-center justify-center gap-2 transition-colors hover:bg-(--color-bg-muted)"
         style={{
@@ -77,22 +78,29 @@ export function UpliftAttachmentPicker({ file, onChange }: UpliftAttachmentPicke
       >
         <Upload size={14} aria-hidden style={{ color: "var(--color-text-muted)" }} />
         <Text as="span" variant="caption" tone="muted">
-          Drag a file here or click to browse
+          Drag files here or click to browse
         </Text>
       </button>
       <input
         ref={inputRef}
         type="file"
+        multiple
         accept="application/pdf,image/jpeg,image/png,.pdf,.jpg,.jpeg,.png"
         hidden
         onChange={(event) => {
-          stageFile(event.target.files);
+          stageFiles(event.target.files);
           event.target.value = "";
         }}
       />
-      {file != null && (
-        <div className="mt-2">
-          <UpliftStagedFile file={file} onRemove={() => onChange(null)} />
+      {files.length > 0 && (
+        <div className="mt-2 flex flex-col gap-1">
+          {files.map((file, index) => (
+            <UpliftStagedFile
+              key={`${file.name}-${file.lastModified}-${index}`}
+              file={file}
+              onRemove={() => onChange(files.filter((_, itemIndex) => itemIndex !== index))}
+            />
+          ))}
         </div>
       )}
     </div>
diff --git a/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-create-form.tsx b/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-create-form.tsx
index 39995a86..77ae243d 100644
--- a/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-create-form.tsx
+++ b/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-create-form.tsx
@@ -13,11 +13,7 @@ import {
 type WorkOrderUpliftCreateFormProps = {
   pending?: boolean;
   remainingAllowance: number;
-  onSubmit: (input: {
-    amount: number;
-    notes: string;
-    file: File | null;
-  }) => void | Promise<unknown>;
+  onSubmit: (input: { amount: number; notes: string; files: File[] }) => void | Promise<unknown>;
 };
 
 function canSubmitUplift(amount: number, notes: string): boolean {
@@ -64,17 +60,17 @@ export function WorkOrderUpliftCreateForm({
 }: WorkOrderUpliftCreateFormProps) {
   const [amount, setAmount] = useState("");
   const [notes, setNotes] = useState("");
-  const [file, setFile] = useState<File | null>(null);
+  const [files, setFiles] = useState<File[]>([]);
   const parsedAmount = Number(amount);
   const helper = upliftAllowanceHelper(parsedAmount, remainingAllowance);
   const canSubmit = canSubmitUplift(parsedAmount, notes);
 
   const handleSubmit = async () => {
     try {
-      await onSubmit({ amount: parsedAmount, notes: notes.trim(), file });
+      await onSubmit({ amount: parsedAmount, notes: notes.trim(), files });
       setAmount("");
       setNotes("");
-      setFile(null);
+      setFiles([]);
     } catch {
       // why: the mutation toasts onError, so a failed submit keeps the typed values.
     }
@@ -113,7 +109,7 @@ export function WorkOrderUpliftCreateForm({
         />
       </div>
 
-      <UpliftAttachmentPicker file={file} onChange={setFile} />
+      <UpliftAttachmentPicker files={files} onChange={setFiles} />
 
       <div className="mt-3 flex justify-end">
         <Button
diff --git a/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-list-item.tsx b/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-list-item.tsx
index 606249a5..bc81057a 100644
--- a/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-list-item.tsx
+++ b/src/app/(protected)/workorders/_components/uplifts/work-order-uplift-list-item.tsx
@@ -75,7 +75,8 @@ function UpliftFiledAttachment({
 }) {
   const hasUrl = file.url !== "";
   const downloadEvidence = () => {
-    void upliftsApi.downloadEvidence(upliftId, file.name).catch((error: unknown) => {
+    const documentId = /^\d+$/.test(file.id) ? file.id : undefined;
+    void upliftsApi.downloadEvidence(upliftId, file.name, documentId).catch((error: unknown) => {
       toast.error(error instanceof Error ? error.message : "Unable to download evidence.");
     });
   };
diff --git a/src/domain/uplifts/api/uplifts-api.ts b/src/domain/uplifts/api/uplifts-api.ts
index fa0a5449..4899bd38 100644
--- a/src/domain/uplifts/api/uplifts-api.ts
+++ b/src/domain/uplifts/api/uplifts-api.ts
@@ -105,8 +105,9 @@ export const upliftsApi = {
   downloadEvidence: async (
     id: string | number,
     fallbackFileName = "uplift-evidence",
+    documentId?: string | number,
   ): Promise<void> => {
-    const response = await fetchEvidence(id, "upliftsApi.downloadEvidence");
+    const response = await fetchEvidence(id, "upliftsApi.downloadEvidence", documentId);
     const blob = await response.blob();
     saveBlob(blob, readContentDispositionFilename(response, fallbackFileName));
   },
@@ -120,8 +121,9 @@ export const upliftsApi = {
     id: string | number,
     tab: Window | null,
     fallbackFileName = "uplift-evidence",
+    documentId?: string | number,
   ): Promise<void> => {
-    const response = await fetchEvidence(id, "upliftsApi.openEvidence");
+    const response = await fetchEvidence(id, "upliftsApi.openEvidence", documentId);
     const blob = await response.blob();
     const type = blob.type.split(";")[0].trim().toLowerCase();
     if (tab == null || !INLINE_EVIDENCE_TYPES.has(type)) {
@@ -145,9 +147,14 @@ const INLINE_EVIDENCE_TYPES = new Set([
 
 const EVIDENCE_URL_TTL_MS = 60_000;
 
-async function fetchEvidence(id: string | number, operation: string): Promise<Response> {
+async function fetchEvidence(
+  id: string | number,
+  operation: string,
+  documentId?: string | number,
+): Promise<Response> {
+  const options = documentId == null ? undefined : { searchParams: { documentId } };
   try {
-    return await apiRequestRaw("get", evidenceUrl(id), undefined, operation);
+    return await apiRequestRaw("get", evidenceUrl(id), options, operation);
   } catch (error) {
     if (error instanceof HTTPError) {
       throw evidenceHttpError(error.response.status);
diff --git a/src/domain/work-orders/api/work-order-uplifts-api.ts b/src/domain/work-orders/api/work-order-uplifts-api.ts
index c37c2e36..c1f4688e 100644
--- a/src/domain/work-orders/api/work-order-uplifts-api.ts
+++ b/src/domain/work-orders/api/work-order-uplifts-api.ts
@@ -46,13 +46,21 @@ export const workOrderUpliftsApi = {
     workOrderId: string | number,
     input: CreateWorkOrderUpliftInput,
   ): Promise<WorkOrderUplift> => {
-    const body: { amount: number; notes: string; evidenceDocumentId?: number } = {
+    const body: {
+      amount: number;
+      notes: string;
+      evidenceDocumentId?: number;
+      evidenceDocumentIds?: number[];
+    } = {
       amount: input.amount,
       notes: input.notes,
     };
     if (input.evidenceDocumentId != null) {
       body.evidenceDocumentId = input.evidenceDocumentId;
     }
+    if (input.evidenceDocumentIds != null && input.evidenceDocumentIds.length > 0) {
+      body.evidenceDocumentIds = input.evidenceDocumentIds;
+    }
     const data = await apiPost<unknown>(API_PATHS.workOrder.uplifts(workOrderId), body);
     return mapWorkOrderUplift(handleApiResponse(data));
   },
diff --git a/src/domain/work-orders/types/work-order-uplift.ts b/src/domain/work-orders/types/work-order-uplift.ts
index 6a213db6..04d39b41 100644
--- a/src/domain/work-orders/types/work-order-uplift.ts
+++ b/src/domain/work-orders/types/work-order-uplift.ts
@@ -39,8 +39,9 @@ export interface WorkOrderUplift {
 export interface CreateWorkOrderUpliftInput {
   amount: number;
   notes: string;
-  file?: File | null;
+  files?: File[];
   evidenceDocumentId?: number;
+  evidenceDocumentIds?: number[];
 }
 
 export const EMPTY_UPLIFT_SUMMARY: UpliftSummary = {
diff --git a/src/domain/work-orders/use-cases/submit-work-order-uplift.ts b/src/domain/work-orders/use-cases/submit-work-order-uplift.ts
index fb3a28d9..02f44973 100644
--- a/src/domain/work-orders/use-cases/submit-work-order-uplift.ts
+++ b/src/domain/work-orders/use-cases/submit-work-order-uplift.ts
@@ -11,6 +11,7 @@ type CreateUpliftBody = {
   amount: number;
   notes: string;
   evidenceDocumentId?: number;
+  evidenceDocumentIds?: number[];
 };
 
 export type SubmitWorkOrderUpliftDeps = {
@@ -62,12 +63,15 @@ export async function submitWorkOrderUplift(
   input: CreateWorkOrderUpliftInput,
   deps: SubmitWorkOrderUpliftDeps,
 ): Promise<WorkOrderUplift> {
-  const evidenceDocumentId = input.file
-    ? await waitForPassedScan(workOrderId, input.file, deps)
-    : undefined;
+  const evidenceDocumentIds: number[] = [];
+  for (const file of input.files ?? []) {
+    evidenceDocumentIds.push(await waitForPassedScan(workOrderId, file, deps));
+  }
+  const [evidenceDocumentId] = evidenceDocumentIds;
   return deps.create(workOrderId, {
     amount: input.amount,
     notes: input.notes,
     evidenceDocumentId,
+    evidenceDocumentIds: evidenceDocumentIds.length > 0 ? evidenceDocumentIds : undefined,
   });
 }
diff --git a/src/test/app/(protected)/workorders/uplift-attachment-picker.test.tsx b/src/test/app/(protected)/workorders/uplift-attachment-picker.test.tsx
new file mode 100644
index 00000000..5470eca3
--- /dev/null
+++ b/src/test/app/(protected)/workorders/uplift-attachment-picker.test.tsx
@@ -0,0 +1,55 @@
+import { useState } from "react";
+import { fireEvent, screen } from "@testing-library/react";
+import { describe, expect, it, vi } from "vitest";
+import { UpliftAttachmentPicker } from "@/app/(protected)/workorders/_components/uplifts/uplift-attachment-picker";
+import { renderWithProviders } from "@/test/test-utils";
+
+function PickerHarness({ onChange }: { onChange: (files: File[]) => void }) {
+  const [files, setFiles] = useState<File[]>([]);
+  return (
+    <UpliftAttachmentPicker
+      files={files}
+      onChange={(next) => {
+        setFiles(next);
+        onChange(next);
+      }}
+    />
+  );
+}
+
+function selectFiles(files: File[]) {
+  const input = document.querySelector('input[type="file"]');
+  fireEvent.change(input as HTMLInputElement, { target: { files } });
+}
+
+describe("UpliftAttachmentPicker", () => {
+  it("keeps every allowed file from one multi-select", () => {
+    const onChange = vi.fn();
+    renderWithProviders(<PickerHarness onChange={onChange} />);
+    const quote = new File(["%PDF"], "quote.pdf", { type: "application/pdf" });
+    const notes = new File(["text"], "notes.txt", { type: "text/plain" });
+    const photo = new File(["jpeg"], "photo.jpg", { type: "image/jpeg" });
+
+    selectFiles([quote, notes, photo]);
+
+    expect(screen.getByText("quote.pdf")).toBeInTheDocument();
+    expect(screen.getByText("photo.jpg")).toBeInTheDocument();
+    expect(screen.queryByText("notes.txt")).not.toBeInTheDocument();
+    expect(onChange).toHaveBeenCalledWith([quote, photo]);
+    expect(document.querySelector('input[type="file"]')?.hasAttribute("multiple")).toBe(true);
+  });
+
+  it("appends a later selection instead of replacing the staged files", () => {
+    const onChange = vi.fn();
+    renderWithProviders(<PickerHarness onChange={onChange} />);
+    const quote = new File(["%PDF"], "quote.pdf", { type: "application/pdf" });
+    const photo = new File(["jpeg"], "photo.jpg", { type: "image/jpeg" });
+
+    selectFiles([quote]);
+    selectFiles([photo]);
+
+    expect(screen.getByText("quote.pdf")).toBeInTheDocument();
+    expect(screen.getByText("photo.jpg")).toBeInTheDocument();
+    expect(onChange).toHaveBeenLastCalledWith([quote, photo]);
+  });
+});
diff --git a/src/test/app/(protected)/workorders/work-order-uplift-evidence-download.test.tsx b/src/test/app/(protected)/workorders/work-order-uplift-evidence-download.test.tsx
new file mode 100644
index 00000000..eceeed7c
--- /dev/null
+++ b/src/test/app/(protected)/workorders/work-order-uplift-evidence-download.test.tsx
@@ -0,0 +1,46 @@
+import { fireEvent, screen } from "@testing-library/react";
+import { describe, expect, it, vi } from "vitest";
+import { WorkOrderUpliftListItem } from "@/app/(protected)/workorders/_components/uplifts/work-order-uplift-list-item";
+import type { WorkOrderUplift } from "@/domain/work-orders/types/work-order-uplift";
+import { renderWithProviders } from "@/test/test-utils";
+
+const downloadEvidence = vi.hoisted(() => vi.fn().mockResolvedValue(undefined));
+
+vi.mock("@/domain/uplifts/api/uplifts-api", () => ({
+  upliftsApi: { downloadEvidence },
+}));
+
+const uplift: WorkOrderUplift = {
+  id: 9,
+  status: "auto_approved",
+  amount: 25,
+  notes: "Leak",
+  requestedAt: "2026-07-20T10:00:00Z",
+  requestedById: "dispatcher-1",
+  requestedByName: "Dispatcher",
+  decidedAt: "",
+  decidedByName: "",
+  decisionNote: "",
+  attachments: [
+    { id: "22", name: "quote.pdf", url: "" },
+    { id: "23", name: "photo.jpg", url: "" },
+  ],
+};
+
+describe("WorkOrderUpliftListItem evidence download", () => {
+  it("downloads each attachment by its document id", () => {
+    renderWithProviders(
+      <WorkOrderUpliftListItem
+        uplift={uplift}
+        readOnly={false}
+        currentUserId="dispatcher-1"
+        currentUserIsAdmin={false}
+      />,
+      { withAuth: false },
+    );
+
+    fireEvent.click(screen.getByRole("button", { name: "photo.jpg" }));
+
+    expect(downloadEvidence).toHaveBeenCalledWith(9, "photo.jpg", "23");
+  });
+});
diff --git a/src/test/domain/uplifts/api/uplifts-api.test.ts b/src/test/domain/uplifts/api/uplifts-api.test.ts
index 656d155e..908e8419 100644
--- a/src/test/domain/uplifts/api/uplifts-api.test.ts
+++ b/src/test/domain/uplifts/api/uplifts-api.test.ts
@@ -43,6 +43,27 @@ describe("upliftsApi", () => {
     await expect(upliftsApi.canApprove(2)).resolves.toBe(false);
   });
 
+  it("requests one linked document when a document id is provided", async () => {
+    apiRequestRaw.mockResolvedValueOnce(
+      new Response("%PDF", {
+        headers: { "Content-Disposition": 'attachment; filename="photo.jpg"' },
+      }),
+    );
+    URL.createObjectURL = vi.fn(() => "blob:evidence");
+    URL.revokeObjectURL = vi.fn();
+    const click = vi.spyOn(HTMLAnchorElement.prototype, "click").mockImplementation(() => {});
+
+    await upliftsApi.downloadEvidence(7, "photo.jpg", 23);
+
+    expect(apiRequestRaw).toHaveBeenCalledWith(
+      "get",
+      "uplifts/7/evidence",
+      { searchParams: { documentId: 23 } },
+      "upliftsApi.downloadEvidence",
+    );
+    click.mockRestore();
+  });
+
   describe("openEvidence", () => {
     function evidenceResponse(body: string, contentType: string): Response {
       return new Response(body, {
diff --git a/src/test/domain/work-orders/api/work-order-uplifts-api.test.ts b/src/test/domain/work-orders/api/work-order-uplifts-api.test.ts
index 941e71a6..71c770c0 100644
--- a/src/test/domain/work-orders/api/work-order-uplifts-api.test.ts
+++ b/src/test/domain/work-orders/api/work-order-uplifts-api.test.ts
@@ -39,6 +39,24 @@ describe("workOrderUpliftsApi", () => {
     });
   });
 
+  it("includes every scanned document id when several files passed", async () => {
+    apiPost.mockResolvedValueOnce({ id: 9, status: "pending", amount: 25, notes: "Leak" });
+
+    await workOrderUpliftsApi.create(7, {
+      amount: 25,
+      notes: "Leak",
+      evidenceDocumentId: 22,
+      evidenceDocumentIds: [22, 23],
+    });
+
+    expect(apiPost).toHaveBeenCalledWith("workorders/7/uplifts", {
+      amount: 25,
+      notes: "Leak",
+      evidenceDocumentId: 22,
+      evidenceDocumentIds: [22, 23],
+    });
+  });
+
   it("uploads one evidence file and reads the pending document id", async () => {
     apiPostForm.mockResolvedValueOnce({
       data: { id: 22, scanStatus: "Pending", originalFileName: "quote.pdf" },
diff --git a/src/test/domain/work-orders/use-cases/submit-work-order-uplift.test.ts b/src/test/domain/work-orders/use-cases/submit-work-order-uplift.test.ts
index ff410055..5afdc03f 100644
--- a/src/test/domain/work-orders/use-cases/submit-work-order-uplift.test.ts
+++ b/src/test/domain/work-orders/use-cases/submit-work-order-uplift.test.ts
@@ -18,13 +18,14 @@ describe("submitWorkOrderUplift", () => {
   it("creates without an evidence id when no file is attached", async () => {
     const collaborators = deps();
 
-    await submitWorkOrderUplift(7, { amount: 25, notes: "Leak", file: null }, collaborators);
+    await submitWorkOrderUplift(7, { amount: 25, notes: "Leak", files: [] }, collaborators);
 
     expect(collaborators.uploadEvidence).not.toHaveBeenCalled();
     expect(collaborators.create).toHaveBeenCalledWith(7, {
       amount: 25,
       notes: "Leak",
       evidenceDocumentId: undefined,
+      evidenceDocumentIds: undefined,
     });
   });
 
@@ -35,13 +36,14 @@ describe("submitWorkOrderUplift", () => {
       getEvidenceStatus: vi.fn().mockResolvedValue({ id: 22, scanStatus: "Passed" }),
     });
 
-    await submitWorkOrderUplift(7, { amount: 25, notes: "Leak", file: quote }, collaborators);
+    await submitWorkOrderUplift(7, { amount: 25, notes: "Leak", files: [quote] }, collaborators);
 
     expect(collaborators.uploadEvidence).toHaveBeenCalledWith(7, quote);
     expect(collaborators.create).toHaveBeenCalledWith(7, {
       amount: 25,
       notes: "Leak",
       evidenceDocumentId: 22,
+      evidenceDocumentIds: [22],
     });
   });
 
@@ -52,7 +54,7 @@ describe("submitWorkOrderUplift", () => {
     });
 
     await expect(
-      submitWorkOrderUplift(7, { amount: 25, notes: "Leak", file: quote }, collaborators),
+      submitWorkOrderUplift(7, { amount: 25, notes: "Leak", files: [quote] }, collaborators),
     ).rejects.toThrow(/rejected/i);
     expect(collaborators.create).not.toHaveBeenCalled();
   });
@@ -65,9 +67,35 @@ describe("submitWorkOrderUplift", () => {
     });
 
     await expect(
-      submitWorkOrderUplift(7, { amount: 25, notes: "Leak", file: quote }, collaborators),
+      submitWorkOrderUplift(7, { amount: 25, notes: "Leak", files: [quote] }, collaborators),
     ).rejects.toThrow(/still being scanned/i);
     expect(collaborators.create).not.toHaveBeenCalled();
     expect(collaborators.sleep).toHaveBeenCalledTimes(30);
   });
+
+  it("uploads every file and sends each passed document id", async () => {
+    const quote = new File(["%PDF"], "quote.pdf", { type: "application/pdf" });
+    const photo = new File(["jpeg"], "photo.jpg", { type: "image/jpeg" });
+    const collaborators = deps({
+      uploadEvidence: vi
+        .fn()
+        .mockResolvedValueOnce({ id: 22, scanStatus: "Passed" })
+        .mockResolvedValueOnce({ id: 23, scanStatus: "Passed" }),
+    });
+
+    await submitWorkOrderUplift(
+      7,
+      { amount: 25, notes: "Leak", files: [quote, photo] },
+      collaborators,
+    );
+
+    expect(collaborators.uploadEvidence).toHaveBeenNthCalledWith(1, 7, quote);
+    expect(collaborators.uploadEvidence).toHaveBeenNthCalledWith(2, 7, photo);
+    expect(collaborators.create).toHaveBeenCalledWith(7, {
+      amount: 25,
+      notes: "Leak",
+      evidenceDocumentId: 22,
+      evidenceDocumentIds: [22, 23],
+    });
+  });
 });