diff --git a/src/api/documents.test.ts b/src/api/documents.test.ts
index 53aaacb..2d2e2d7 100644
--- a/src/api/documents.test.ts
+++ b/src/api/documents.test.ts
@@ -1,5 +1,11 @@
 import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
-import { fetchDocuments, patchWorkerDocument, registerWorkerDocument } from './documents'
+import {
+  fetchDocumentRequestDraft,
+  fetchDocuments,
+  patchWorkerDocument,
+  registerWorkerDocument,
+  upsertDocumentRequestDraft,
+} from './documents'
 
 function jsonResponse(body: unknown) {
   return new Response(JSON.stringify(body), { status: 200, headers: { 'Content-Type': 'application/json' } })
@@ -87,3 +93,55 @@ describe('patchWorkerDocument', () => {
     expect(init?.method).toBe('PATCH')
   })
 })
+
+describe('document request draft', () => {
+  it('GETs the saved content and version for recovery', async () => {
+    vi.mocked(fetch).mockResolvedValueOnce(
+      jsonResponse({
+        draft_id: 'draft-1',
+        language: 'vi',
+        document_types: ['PASSPORT_COPY', 'CONTRACT'],
+        message: 'Vui lòng nộp hồ sơ.',
+        version: 3,
+        review_status: 'DRAFT',
+        updated_at: '2026-08-08T00:00:00Z',
+      }),
+    )
+
+    const draft = await fetchDocumentRequestDraft('T/1')
+
+    expect(draft.version).toBe(3)
+    const [url, init] = vi.mocked(fetch).mock.calls[0]
+    expect(url).toContain('/tasks/T%2F1/document-request-draft')
+    expect(init?.method).toBeUndefined()
+  })
+
+  it('PUTs the restored expected version with the edited message', async () => {
+    vi.mocked(fetch).mockResolvedValueOnce(
+      jsonResponse({
+        draft_id: 'draft-1',
+        language: 'ko',
+        document_types: ['ARC'],
+        message: '외국인등록증을 제출해 주세요.',
+        version: 2,
+        review_status: 'DRAFT',
+        updated_at: '2026-08-08T00:00:00Z',
+      }),
+    )
+
+    await upsertDocumentRequestDraft('T/1', {
+      language: 'ko',
+      document_types: ['ARC'],
+      message: '외국인등록증을 제출해 주세요.',
+      expected_version: 1,
+    })
+
+    const [url, init] = vi.mocked(fetch).mock.calls[0]
+    expect(url).toContain('/tasks/T%2F1/document-request-draft')
+    expect(init?.method).toBe('PUT')
+    expect(JSON.parse(String(init?.body))).toMatchObject({
+      message: '외국인등록증을 제출해 주세요.',
+      expected_version: 1,
+    })
+  })
+})
diff --git a/src/api/documents.ts b/src/api/documents.ts
index ab7db38..6a52985 100644
--- a/src/api/documents.ts
+++ b/src/api/documents.ts
@@ -65,12 +65,22 @@ export interface DocumentRequestUpsertBody {
 
 export interface DocumentRequestDraftResponse {
   draft_id: string
+  language: string
+  document_types: DocumentType[]
+  message: string | null
   version: number
   review_status: string
+  updated_at: string
+}
+
+export function fetchDocumentRequestDraft(taskId: string): Promise<DocumentRequestDraftResponse> {
+  return apiFetch<DocumentRequestDraftResponse>(
+    `/tasks/${encodeURIComponent(taskId)}/document-request-draft`,
+  )
 }
 
-// 초안 저장만 하고 실제 발송·Worker Link 생성은 하지 않는다 (#176 스코프 아님).
-// 최초 생성 시 expected_version은 관례상 0을 보낸다.
+// 초안 저장만 하고 실제 발송·Worker Link 생성은 하지 않는다. 최초 생성 시
+// expected_version은 0, 이후에는 fetchDocumentRequestDraft가 반환한 최신 version을 보낸다.
 export function upsertDocumentRequestDraft(
   taskId: string,
   body: DocumentRequestUpsertBody,
diff --git a/src/api/workerLinks.ts b/src/api/workerLinks.ts
index b4e5fde..0f5802f 100644
--- a/src/api/workerLinks.ts
+++ b/src/api/workerLinks.ts
@@ -1,4 +1,5 @@
 import { apiFetch } from './client'
+import type { DocumentType } from './documents'
 
 export type WorkerResponseType =
   | 'ACKNOWLEDGED'
@@ -19,7 +20,9 @@ export interface WorkerLinkIssueResponse {
 
 export interface WorkerLinkViewResponse {
   guidance: string
+  language: string
   due_date: string | null
+  requested_document_types: DocumentType[]
   allowed_responses: WorkerResponseType[]
 }
 
diff --git a/src/pages/CaseDetailPage/CaseDetailPage.module.css b/src/pages/CaseDetailPage/CaseDetailPage.module.css
index 2ae76e7..4c59ee0 100644
--- a/src/pages/CaseDetailPage/CaseDetailPage.module.css
+++ b/src/pages/CaseDetailPage/CaseDetailPage.module.css
@@ -406,6 +406,143 @@
   color: var(--text-secondary);
 }
 
+.documentRequestStatus {
+  margin: 16px 0 0;
+  color: var(--text-secondary);
+  font-size: 13px;
+}
+
+.documentRequestError {
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  gap: 16px;
+  margin-top: 16px;
+  padding: var(--fowoco-spacing-12) var(--fowoco-spacing-16);
+  background: var(--fowoco-red-50);
+  border-radius: var(--fowoco-radius-8);
+}
+
+.documentRequestError p {
+  margin: 0;
+  color: var(--status-critical);
+  font-size: 13px;
+}
+
+.documentRequestError button {
+  flex-shrink: 0;
+  padding: 0;
+  background: none;
+  border: none;
+  color: var(--status-critical);
+  font-size: 13px;
+  font-weight: 700;
+  cursor: pointer;
+}
+
+.documentRequestCard {
+  margin-top: 16px;
+  padding: var(--fowoco-spacing-20) var(--fowoco-spacing-24);
+  background: var(--surface-default);
+  border: 1px solid var(--border-default);
+  border-radius: var(--fowoco-radius-8);
+}
+
+.documentRequestHeader,
+.documentRequestFooter {
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  gap: 16px;
+}
+
+.documentRequestEyebrow {
+  margin: 0 0 4px;
+  color: var(--brand-primary);
+  font-size: 12px;
+  font-weight: 700;
+}
+
+.documentRequestTitle {
+  margin: 0;
+  color: var(--text-primary);
+  font-size: 16px;
+}
+
+.documentRequestVersion {
+  color: var(--text-secondary);
+  font-size: 12px;
+}
+
+.documentRequestTypes {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 8px;
+  margin-top: 16px;
+}
+
+.documentRequestTypes span {
+  padding: 6px 10px;
+  background: var(--surface-subtle);
+  border-radius: 999px;
+  color: var(--text-secondary);
+  font-size: 12px;
+}
+
+.documentRequestLabel {
+  display: block;
+  margin: 18px 0 8px;
+  color: var(--text-primary);
+  font-size: 13px;
+  font-weight: 600;
+}
+
+.documentRequestSelect,
+.documentRequestTextarea {
+  width: 100%;
+  padding: 10px 12px;
+  background: var(--surface-default);
+  border: 1px solid var(--border-default);
+  border-radius: var(--fowoco-radius-8);
+  color: var(--text-primary);
+  font: inherit;
+}
+
+.documentRequestTextarea {
+  min-height: 104px;
+  line-height: 1.6;
+  resize: vertical;
+}
+
+.documentRequestSelect:focus-visible,
+.documentRequestTextarea:focus-visible {
+  outline: 2px solid var(--brand-primary);
+  outline-offset: 2px;
+}
+
+.documentRequestFooter {
+  margin-top: 12px;
+  color: var(--text-secondary);
+  font-size: 12px;
+}
+
+.documentRequestAction {
+  min-height: 40px;
+  padding: 0 16px;
+  background: var(--brand-primary);
+  border: none;
+  border-radius: var(--fowoco-radius-8);
+  color: var(--fowoco-white);
+  font-size: 13px;
+  font-weight: 700;
+  cursor: pointer;
+}
+
+.documentRequestAction:disabled {
+  cursor: wait;
+  opacity: 0.6;
+}
+
 .commList {
   display: flex;
   flex-direction: column;
diff --git a/src/pages/CaseDetailPage/CaseDetailPage.test.tsx b/src/pages/CaseDetailPage/CaseDetailPage.test.tsx
index 02167db..ac68c6f 100644
--- a/src/pages/CaseDetailPage/CaseDetailPage.test.tsx
+++ b/src/pages/CaseDetailPage/CaseDetailPage.test.tsx
@@ -7,9 +7,11 @@ import type {
   DocumentItemResponse,
   DocumentPageResponse,
   DocumentReadinessResponse,
+  DocumentRequestDraftResponse,
 } from '../../api/documents'
 import type { TaskDetailResponse } from '../../api/tasks'
 import { ToastViewport } from '../../components/ui/ToastViewport/ToastViewport'
+import { useAuthStore } from '../../store/authStore'
 import { useToastStore } from '../../store/toastStore'
 import { CaseDetailPage } from './CaseDetailPage'
 import { CASE_COMMUNICATION, CASE_TABS, CONTEXT_DRAWER } from './caseDetailData'
@@ -124,16 +126,44 @@ function mockTaskAndActivities(
   activities: AuditEventResponse[] = [],
   readinessOverrides: Partial<DocumentReadinessResponse> = {},
   documents: DocumentItemResponse[] = [],
+  savedDocumentRequestDraft: DocumentRequestDraftResponse | null = null,
 ) {
-  vi.mocked(fetch).mockImplementation((input) => {
+  let currentDocumentRequestDraft = savedDocumentRequestDraft
+  vi.mocked(fetch).mockImplementation((input, init) => {
     const url = String(input)
     if (url.includes('/activities')) return Promise.resolve(jsonResponse(activities))
     if (url.includes('/document-readiness'))
       return Promise.resolve(jsonResponse(readinessResponse(readinessOverrides)))
     if (url.includes('/document-request-draft')) {
-      return Promise.resolve(
-        jsonResponse({ draft_id: 'draft-1', version: 1, review_status: 'PENDING' }),
-      )
+      if (init?.method !== 'PUT') {
+        return Promise.resolve(
+          currentDocumentRequestDraft
+            ? jsonResponse(currentDocumentRequestDraft)
+            : errorResponse(404, 'DOCUMENT_REQUEST_DRAFT_NOT_FOUND', '초안 없음'),
+        )
+      }
+      const body = JSON.parse(String(init.body)) as {
+        language: string
+        document_types: DocumentRequestDraftResponse['document_types']
+        message: string
+        expected_version: number
+      }
+      if (
+        currentDocumentRequestDraft &&
+        body.expected_version !== currentDocumentRequestDraft.version
+      ) {
+        return Promise.resolve(errorResponse(409, 'VERSION_CONFLICT', '초안 버전 충돌'))
+      }
+      currentDocumentRequestDraft = {
+        draft_id: currentDocumentRequestDraft?.draft_id ?? 'draft-1',
+        language: body.language,
+        document_types: body.document_types,
+        message: body.message,
+        version: currentDocumentRequestDraft ? currentDocumentRequestDraft.version + 1 : 0,
+        review_status: 'DRAFT',
+        updated_at: '2026-08-08T00:00:00Z',
+      }
+      return Promise.resolve(jsonResponse(currentDocumentRequestDraft))
     }
     if (url.includes('/documents?'))
       return Promise.resolve(jsonResponse(documentsResponse(documents)))
@@ -197,6 +227,7 @@ function mockTaskError(status: number, code: string, message: string) {
 }
 
 beforeEach(() => {
+  useAuthStore.setState({ user: null, status: 'ready' })
   useToastStore.setState({ toasts: [] })
   vi.stubGlobal('fetch', vi.fn())
 })
@@ -338,9 +369,63 @@ describe('CaseDetailPage', () => {
     expect(await screen.findByText('누락 1건 · 만료 0건')).toBeInTheDocument()
 
     await user.click(screen.getByRole('tab', { name: CASE_TABS[2] }))
-    await user.click(await screen.findByRole('button', { name: '요청 초안 저장 →' }))
+    await user.click(await screen.findByRole('button', { name: '요청 초안 저장' }))
 
     expect(await screen.findByText('서류 요청 초안을 저장했습니다.')).toBeInTheDocument()
+    const saveCall = vi.mocked(fetch).mock.calls.find(
+      ([url, init]) =>
+        String(url).includes('/document-request-draft') && init?.method === 'PUT',
+    )
+    expect(JSON.parse(String(saveCall?.[1]?.body))).toMatchObject({
+      document_types: ['ARC'],
+      message: '다음 서류를 제출해 주세요: 외국인등록증.',
+      expected_version: 0,
+    })
+  })
+
+  it('restores and updates a saved document request draft', async () => {
+    const user = userEvent.setup()
+    mockTaskAndActivities(
+      {},
+      [],
+      { missing: ['ARC'], completion_blocked: true },
+      [],
+      {
+        draft_id: 'draft-1',
+        language: 'vi',
+        document_types: ['PASSPORT_COPY', 'CONTRACT'],
+        message: 'Vui lòng nộp hộ chiếu và hợp đồng lao động.',
+        version: 3,
+        review_status: 'DRAFT',
+        updated_at: '2026-08-08T00:00:00Z',
+      },
+    )
+    renderPage()
+    await screen.findByText('응웬반A 체류연장 준비')
+    await user.click(screen.getByRole('tab', { name: CASE_TABS[2] }))
+
+    expect(await screen.findByDisplayValue('Vui lòng nộp hộ chiếu và hợp đồng lao động.')).toBeInTheDocument()
+    expect(screen.getByLabelText('안내 언어')).toHaveValue('vi')
+    expect(screen.getByText('저장본 v3')).toBeInTheDocument()
+
+    const message = screen.getByLabelText('근로자 안내문')
+    await user.clear(message)
+    await user.type(message, '수정된 안내문')
+    await user.click(screen.getByRole('button', { name: '요청 초안 저장' }))
+
+    const updateCall = await waitFor(() => {
+      const call = vi.mocked(fetch).mock.calls.find(
+        ([url, init]) =>
+          String(url).includes('/document-request-draft') && init?.method === 'PUT',
+      )
+      expect(call).toBeDefined()
+      return call!
+    })
+    expect(JSON.parse(String(updateCall[1]?.body))).toMatchObject({
+      message: '수정된 안내문',
+      expected_version: 3,
+    })
+    expect(await screen.findByText('저장본 v4')).toBeInTheDocument()
   })
 
   it('switches to the communication tab and shows message content', async () => {
diff --git a/src/pages/CaseDetailPage/CaseDetailPage.tsx b/src/pages/CaseDetailPage/CaseDetailPage.tsx
index a469628..97fbde3 100644
--- a/src/pages/CaseDetailPage/CaseDetailPage.tsx
+++ b/src/pages/CaseDetailPage/CaseDetailPage.tsx
@@ -11,9 +11,12 @@ import {
 } from '../../api/approvals'
 import { fetchTaskActivities } from '../../api/audit'
 import {
+  fetchDocumentRequestDraft,
   fetchDocumentReadiness,
   fetchDocuments,
   upsertDocumentRequestDraft,
+  type DocumentRequestDraftResponse,
+  type DocumentType,
 } from '../../api/documents'
 import { ApiError, getErrorMessage } from '../../api/errors'
 import { cancelTask, fetchTaskById, updateChecklistItem } from '../../api/tasks'
@@ -27,9 +30,11 @@ import { EmptyState } from '../../components/ui/EmptyState/EmptyState'
 import { StatusLabel, type StatusTone } from '../../components/ui/StatusLabel/StatusLabel'
 import { Tabs } from '../../components/ui/Tabs/Tabs'
 import { useApiQuery } from '../../hooks/useApiQuery'
+import { useAuthStore } from '../../store/authStore'
 import { useToastStore } from '../../store/toastStore'
 import { ACTOR_TYPE_TO_AGENT_SOURCE, AUDIT_ACTION_LABEL } from '../../utils/auditLabels'
 import { formatEventTime } from '../../utils/datetime'
+import { DOCUMENT_TYPE_LABEL } from '../../utils/documentLabels'
 import { TASK_SOURCE_LABEL, TASK_STATUS_LABEL, TASK_STATUS_TONE } from '../../utils/taskStatus'
 import { getDocumentViewModel } from '../../view-models/documentViewModel'
 import { getOperationalDateViewModel } from '../../view-models/dateViewModel'
@@ -65,6 +70,53 @@ const EVIDENCE_TYPE_BY_LABEL: Record<string, EvidenceType> = {
   '화면 캡처': 'OFFICIAL_RESULT',
 }
 
+interface DocumentRequestDraftForm {
+  taskId: string
+  language: string
+  documentTypes: DocumentType[]
+  message: string
+}
+
+const GUIDANCE_LANGUAGES = [
+  { value: 'ko', label: '한국어' },
+  { value: 'vi', label: '베트남어' },
+  { value: 'en', label: '영어' },
+  { value: 'zh', label: '중국어' },
+  { value: 'th', label: '태국어' },
+  { value: 'id', label: '인도네시아어' },
+  { value: 'km', label: '크메르어' },
+  { value: 'mn', label: '몽골어' },
+  { value: 'uz', label: '우즈베크어' },
+  { value: 'ne', label: '네팔어' },
+]
+
+function uniqueDocumentTypes(types: DocumentType[]): DocumentType[] {
+  return [...new Set(types)]
+}
+
+function defaultDocumentRequestMessage(documentTypes: DocumentType[]): string {
+  if (documentTypes.length === 0) return ''
+  return `다음 서류를 제출해 주세요: ${documentTypes
+    .map((type) => DOCUMENT_TYPE_LABEL[type])
+    .join(', ')}.`
+}
+
+async function fetchDocumentRequestDraftOrNull(
+  taskId: string,
+): Promise<DocumentRequestDraftResponse | null> {
+  try {
+    return await fetchDocumentRequestDraft(taskId)
+  } catch (error) {
+    if (
+      error instanceof ApiError &&
+      (error.status === 404 || error.code === 'DOCUMENT_REQUEST_DRAFT_NOT_FOUND')
+    ) {
+      return null
+    }
+    throw error
+  }
+}
+
 export function CaseDetailPage() {
   const { taskId } = useParams()
   const [activeTab, setActiveTab] = useState(CASE_TABS[0])
@@ -78,7 +130,15 @@ export function CaseDetailPage() {
   const [lastReissue, setLastReissue] = useState<ReissueSubmission | null>(null)
   const [issuedWorkerUrl, setIssuedWorkerUrl] = useState<string | null>(null)
   const [issuedExpiresAt, setIssuedExpiresAt] = useState<string | null>(null)
+  const [savingDocumentRequestDraft, setSavingDocumentRequestDraft] = useState(false)
+  const [documentRequestDraftForm, setDocumentRequestDraftForm] =
+    useState<DocumentRequestDraftForm | null>(null)
+  const [documentRequestDraftVersion, setDocumentRequestDraftVersion] = useState<{
+    taskId: string
+    version: number
+  } | null>(null)
   const moreMenuRef = useRef<HTMLDivElement>(null)
+  const userRole = useAuthStore((state) => state.user?.role)
   const showToast = useToastStore((state) => state.showToast)
 
   const taskFetcher = useCallback(() => fetchTaskById(taskId ?? ''), [taskId])
@@ -96,6 +156,44 @@ export function CaseDetailPage() {
   const readinessFetcher = useCallback(() => fetchDocumentReadiness(taskId ?? ''), [taskId])
   const { data: readiness } = useApiQuery(readinessFetcher)
 
+  const documentRequestDraftFetcher = useCallback(() => {
+    if (!taskId || userRole === 'VIEWER') return Promise.resolve(null)
+    return fetchDocumentRequestDraftOrNull(taskId)
+  }, [taskId, userRole])
+  const {
+    status: documentRequestDraftStatus,
+    data: documentRequestDraft,
+    error: documentRequestDraftError,
+    refetch: refetchDocumentRequestDraft,
+  } = useApiQuery(
+    documentRequestDraftFetcher,
+    useCallback((draft: DocumentRequestDraftResponse | null) => draft === null, []),
+  )
+
+  useEffect(() => {
+    if (!taskId || !readiness || documentRequestDraftStatus === 'loading') return
+    if (documentRequestDraftStatus === 'error') return
+
+    setDocumentRequestDraftForm((current) => {
+      if (current?.taskId === taskId) return current
+      const documentTypes = documentRequestDraft
+        ? documentRequestDraft.document_types
+        : uniqueDocumentTypes([...readiness.missing, ...readiness.expired])
+      return {
+        taskId,
+        language: documentRequestDraft?.language ?? 'ko',
+        documentTypes,
+        message:
+          documentRequestDraft?.message ?? defaultDocumentRequestMessage(documentTypes),
+      }
+    })
+    setDocumentRequestDraftVersion(
+      documentRequestDraft
+        ? { taskId, version: documentRequestDraft.version }
+        : null,
+    )
+  }, [documentRequestDraft, documentRequestDraftStatus, readiness, taskId])
+
   const workerId = task?.worker_id
   const documentsFetcher = useCallback(() => {
     if (!workerId) return Promise.resolve({ items: [], page: 0, size: 0, total_elements: 0 })
@@ -260,16 +358,40 @@ export function CaseDetailPage() {
   }
 
   async function handleSaveDocumentRequestDraft() {
-    if (!task || !readiness) return
+    if (!task || !documentRequestDraftForm || savingDocumentRequestDraft) return
+    const message = documentRequestDraftForm.message.trim()
+    if (!message) {
+      showToast('근로자에게 표시할 안내문을 입력해 주세요.')
+      return
+    }
+    if (documentRequestDraftForm.documentTypes.length === 0) {
+      showToast('요청할 서류가 없습니다.')
+      return
+    }
+    setSavingDocumentRequestDraft(true)
     try {
-      await upsertDocumentRequestDraft(task.task_id, {
-        language: 'ko',
-        document_types: [...readiness.missing, ...readiness.expired],
-        expected_version: 0,
+      const savedDraft = await upsertDocumentRequestDraft(task.task_id, {
+        language: documentRequestDraftForm.language,
+        document_types: documentRequestDraftForm.documentTypes,
+        message,
+        expected_version:
+          documentRequestDraftVersion?.taskId === task.task_id
+            ? documentRequestDraftVersion.version
+            : 0,
       })
+      setDocumentRequestDraftVersion({ taskId: task.task_id, version: savedDraft.version })
+      setDocumentRequestDraftForm((current) =>
+        current?.taskId === task.task_id ? { ...current, message } : current,
+      )
       showToast('서류 요청 초안을 저장했습니다.')
-    } catch {
-      showToast('서류 요청 초안을 저장하지 못했습니다.')
+    } catch (error) {
+      showToast(
+        error instanceof ApiError
+          ? getErrorMessage(error)
+          : '서류 요청 초안을 저장하지 못했습니다.',
+      )
+    } finally {
+      setSavingDocumentRequestDraft(false)
     }
   }
 
@@ -692,15 +814,109 @@ export function CaseDetailPage() {
               })}
             </div>
           )}
-          {readiness && (readiness.missing.length > 0 || readiness.expired.length > 0) && (
-            <button
-              type="button"
-              className={styles.contextLink}
-              onClick={handleSaveDocumentRequestDraft}
-            >
-              요청 초안 저장 →
-            </button>
+          {userRole !== 'VIEWER' && documentRequestDraftStatus === 'loading' && (
+            <p className={styles.documentRequestStatus} role="status">
+              저장된 요청 초안을 확인하고 있습니다.
+            </p>
           )}
+          {userRole !== 'VIEWER' && documentRequestDraftStatus === 'error' && (
+            <div className={styles.documentRequestError} role="alert">
+              <p>
+                {documentRequestDraftError
+                  ? getErrorMessage(documentRequestDraftError)
+                  : '저장된 요청 초안을 불러오지 못했습니다.'}
+              </p>
+              <button type="button" onClick={refetchDocumentRequestDraft}>
+                다시 시도
+              </button>
+            </div>
+          )}
+          {userRole !== 'VIEWER' &&
+            documentRequestDraftStatus !== 'error' &&
+            documentRequestDraftForm?.taskId === task.task_id &&
+            documentRequestDraftForm.documentTypes.length > 0 && (
+              <section className={styles.documentRequestCard} aria-labelledby="document-request-title">
+                <div className={styles.documentRequestHeader}>
+                  <div>
+                    <p className={styles.documentRequestEyebrow}>근로자 모바일 요청</p>
+                    <h2 id="document-request-title" className={styles.documentRequestTitle}>
+                      서류 요청 초안
+                    </h2>
+                  </div>
+                  <span className={styles.documentRequestVersion}>
+                    {documentRequestDraftVersion?.taskId === task.task_id
+                      ? `저장본 v${documentRequestDraftVersion.version}`
+                      : '새 초안'}
+                  </span>
+                </div>
+
+                <div className={styles.documentRequestTypes} aria-label="요청 서류">
+                  {documentRequestDraftForm.documentTypes.map((type) => (
+                    <span key={type}>{DOCUMENT_TYPE_LABEL[type]}</span>
+                  ))}
+                </div>
+
+                <label className={styles.documentRequestLabel} htmlFor="document-request-language">
+                  안내 언어
+                </label>
+                <select
+                  id="document-request-language"
+                  className={styles.documentRequestSelect}
+                  value={documentRequestDraftForm.language}
+                  onChange={(event) =>
+                    setDocumentRequestDraftForm((current) =>
+                      current?.taskId === task.task_id
+                        ? { ...current, language: event.target.value }
+                        : current,
+                    )
+                  }
+                >
+                  {!GUIDANCE_LANGUAGES.some(
+                    (language) => language.value === documentRequestDraftForm.language,
+                  ) && (
+                    <option value={documentRequestDraftForm.language}>
+                      {documentRequestDraftForm.language}
+                    </option>
+                  )}
+                  {GUIDANCE_LANGUAGES.map((language) => (
+                    <option key={language.value} value={language.value}>
+                      {language.label}
+                    </option>
+                  ))}
+                </select>
+
+                <label className={styles.documentRequestLabel} htmlFor="document-request-message">
+                  근로자 안내문
+                </label>
+                <textarea
+                  id="document-request-message"
+                  className={styles.documentRequestTextarea}
+                  maxLength={1000}
+                  rows={4}
+                  value={documentRequestDraftForm.message}
+                  onChange={(event) =>
+                    setDocumentRequestDraftForm((current) =>
+                      current?.taskId === task.task_id
+                        ? { ...current, message: event.target.value }
+                        : current,
+                    )
+                  }
+                />
+
+                <div className={styles.documentRequestFooter}>
+                  <span>{documentRequestDraftForm.message.length}/1000</span>
+                  <button
+                    type="button"
+                    className={styles.documentRequestAction}
+                    disabled={savingDocumentRequestDraft}
+                    aria-busy={savingDocumentRequestDraft}
+                    onClick={handleSaveDocumentRequestDraft}
+                  >
+                    {savingDocumentRequestDraft ? '저장 중…' : '요청 초안 저장'}
+                  </button>
+                </div>
+              </section>
+            )}
         </div>
       )}
 
diff --git a/src/pages/LinkRequestPage/LinkRequestPage.module.css b/src/pages/LinkRequestPage/LinkRequestPage.module.css
index b30398b..d5f7d29 100644
--- a/src/pages/LinkRequestPage/LinkRequestPage.module.css
+++ b/src/pages/LinkRequestPage/LinkRequestPage.module.css
@@ -40,6 +40,12 @@
   color: var(--status-warning);
 }
 
+.language {
+  margin: 6px 0 0;
+  color: var(--text-secondary);
+  font-size: 12px;
+}
+
 .divider {
   margin: 20px 0;
   border: none;
@@ -53,6 +59,39 @@
   color: var(--text-primary);
 }
 
+.requestedDocuments {
+  margin-top: 24px;
+  padding: 16px 20px;
+  background: var(--surface-subtle);
+  border: 1px solid var(--border-default);
+  border-radius: var(--fowoco-radius-8);
+}
+
+.requestedDocumentsTitle {
+  margin: 0;
+  color: var(--text-primary);
+  font-size: 13px;
+  font-weight: 700;
+}
+
+.requestedDocumentsList {
+  display: flex;
+  flex-wrap: wrap;
+  gap: 8px;
+  margin: 12px 0 0;
+  padding: 0;
+  list-style: none;
+}
+
+.requestedDocumentsList li {
+  padding: 6px 10px;
+  background: var(--surface-default);
+  border: 1px solid var(--border-default);
+  border-radius: 999px;
+  color: var(--text-primary);
+  font-size: 12px;
+}
+
 .privacy {
   min-height: 96px;
   margin: 30px 0 0;
diff --git a/src/pages/LinkRequestPage/LinkRequestPage.test.tsx b/src/pages/LinkRequestPage/LinkRequestPage.test.tsx
index f66a7f8..bf1dab7 100644
--- a/src/pages/LinkRequestPage/LinkRequestPage.test.tsx
+++ b/src/pages/LinkRequestPage/LinkRequestPage.test.tsx
@@ -13,7 +13,9 @@ function jsonResponse(body: unknown, status = 200) {
 
 const VIEW = {
   guidance: '여권 사진면 사본을 제출해 주세요.',
+  language: 'vi',
   due_date: '2026-08-10',
+  requested_document_types: ['PASSPORT_COPY', 'CONTRACT'],
   allowed_responses: ['ACKNOWLEDGED', 'QUESTION', 'DOCUMENT_SUBMITTED'],
 }
 
@@ -33,6 +35,31 @@ describe('LinkRequestPage', () => {
 
     expect(await screen.findByText('여권 사진면 사본을 제출해 주세요.')).toBeInTheDocument()
     expect(screen.getByText(/2026.08.10/)).toBeInTheDocument()
+    expect(screen.getByText('베트남어 안내')).toBeInTheDocument()
+    expect(screen.getByText('제출할 서류 2개')).toBeInTheDocument()
+    expect(screen.getByText('근로계약서')).toBeInTheDocument()
+  })
+
+  it('shows a retryable preparing state for a link without ready draft content', async () => {
+    vi.mocked(fetch).mockResolvedValue(jsonResponse({
+      timestamp: '2026-08-08T00:00:00Z',
+      status: 409,
+      code: 'WORKER_LINK_CONTENT_NOT_READY',
+      message: '근로자에게 표시할 요청 안내가 아직 준비되지 않았습니다.',
+      path: '/api/v1/public/worker-links/token-1',
+      request_id: 'request-1',
+      field_errors: [],
+    }, 409))
+    render(
+      <MemoryRouter initialEntries={['/worker-portal/token-1']}>
+        <Routes>
+          <Route path="/worker-portal/:token" element={<LinkRequestPage />} />
+        </Routes>
+      </MemoryRouter>,
+    )
+
+    expect(await screen.findByText('요청 내용을 준비하고 있습니다')).toBeInTheDocument()
+    expect(screen.getByRole('button', { name: '다시 시도' })).toBeInTheDocument()
   })
 
   it('keeps the token when navigating to the upload page', async () => {
diff --git a/src/pages/LinkRequestPage/LinkRequestPage.tsx b/src/pages/LinkRequestPage/LinkRequestPage.tsx
index 920ab41..16fd7e8 100644
--- a/src/pages/LinkRequestPage/LinkRequestPage.tsx
+++ b/src/pages/LinkRequestPage/LinkRequestPage.tsx
@@ -5,9 +5,23 @@ import { fetchWorkerLink, submitWorkerResponse } from '../../api/workerLinks'
 import { MobileShell } from '../../components/mobile/MobileShell'
 import { EmptyState } from '../../components/ui/EmptyState/EmptyState'
 import { useApiQuery } from '../../hooks/useApiQuery'
+import { DOCUMENT_TYPE_LABEL } from '../../utils/documentLabels'
 import { getOperationalDateViewModel } from '../../view-models/dateViewModel'
 import styles from './LinkRequestPage.module.css'
 
+const LANGUAGE_LABEL: Record<string, string> = {
+  ko: '한국어',
+  vi: '베트남어',
+  en: '영어',
+  zh: '중국어',
+  th: '태국어',
+  id: '인도네시아어',
+  km: '크메르어',
+  mn: '몽골어',
+  uz: '우즈베크어',
+  ne: '네팔어',
+}
+
 export function LinkRequestPage() {
   const { token } = useParams()
 
@@ -98,13 +112,19 @@ function WorkerLinkRequest({ token }: { token: string }) {
   }
 
   if (status === 'error' || !data) {
+    const contentNotReady =
+      error instanceof ApiError && error.code === 'WORKER_LINK_CONTENT_NOT_READY'
     return (
       <MobileShell right={<span>보안 링크</span>}>
         <EmptyState
           kind="error"
-          title="요청 내용을 불러오지 못했습니다"
+          title={contentNotReady ? '요청 내용을 준비하고 있습니다' : '요청 내용을 불러오지 못했습니다'}
           body={
-            error instanceof ApiError ? getErrorMessage(error) : '네트워크 상태를 확인해 주세요.'
+            contentNotReady
+              ? '회사 담당자가 안내문을 준비 중입니다. 잠시 후 같은 링크에서 다시 확인해 주세요.'
+              : error instanceof ApiError
+                ? getErrorMessage(error)
+                : '네트워크 상태를 확인해 주세요.'
           }
           actionLabel="다시 시도"
           onAction={refetch}
@@ -114,6 +134,7 @@ function WorkerLinkRequest({ token }: { token: string }) {
   }
 
   const due = getOperationalDateViewModel('TASK_DUE', data.due_date)
+  const requestedDocumentTypes = [...new Set(data.requested_document_types)]
   const canContinue =
     data.allowed_responses.includes('ACKNOWLEDGED') ||
     data.allowed_responses.includes('DOCUMENT_SUBMITTED')
@@ -133,11 +154,23 @@ function WorkerLinkRequest({ token }: { token: string }) {
         확인해 주세요
       </h1>
       <p className={styles.deadline}>{due.display}</p>
+      <p className={styles.language}>{LANGUAGE_LABEL[data.language] ?? data.language} 안내</p>
 
       <hr className={styles.divider} />
 
       <p className={styles.body}>{data.guidance}</p>
 
+      <section className={styles.requestedDocuments} aria-labelledby="requested-documents-title">
+        <p id="requested-documents-title" className={styles.requestedDocumentsTitle}>
+          제출할 서류 {requestedDocumentTypes.length}개
+        </p>
+        <ul className={styles.requestedDocumentsList}>
+          {requestedDocumentTypes.map((type) => (
+            <li key={type}>{DOCUMENT_TYPE_LABEL[type]}</li>
+          ))}
+        </ul>
+      </section>
+
       <div className={styles.privacy}>
         <p className={styles.privacyTitle}>이 업무에 필요한 정보만 표시됩니다.</p>
         <p className={styles.privacyBody}>선택한 파일은 이 보안 링크의 업무에만 연결됩니다.</p>
diff --git a/src/pages/LinkUploadPage/LinkUploadPage.module.css b/src/pages/LinkUploadPage/LinkUploadPage.module.css
index 9c40bc9..91859e5 100644
--- a/src/pages/LinkUploadPage/LinkUploadPage.module.css
+++ b/src/pages/LinkUploadPage/LinkUploadPage.module.css
@@ -13,11 +13,43 @@
   color: var(--text-secondary);
 }
 
+.requestList {
+  display: flex;
+  flex-direction: column;
+  gap: 16px;
+  margin-top: 24px;
+}
+
+.requestCard {
+  padding: 16px;
+  background: var(--surface-subtle);
+  border: 1px solid var(--border-default);
+  border-radius: var(--fowoco-radius-10);
+}
+
+.requestCardHeader {
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  gap: 12px;
+}
+
+.requestCardHeader span {
+  color: var(--text-secondary);
+  font-size: 12px;
+}
+
+.requestTitle {
+  margin: 0;
+  color: var(--text-primary);
+  font-size: 15px;
+}
+
 .dropzone {
   width: 100%;
-  min-height: 148px;
-  margin-top: 20px;
-  padding: 20px;
+  min-height: 124px;
+  margin-top: 12px;
+  padding: 16px;
   background: var(--surface-default);
   border: 2px solid var(--brand-primary);
   border-radius: var(--fowoco-radius-8);
@@ -138,6 +170,11 @@
   cursor: pointer;
 }
 
+.removeFile:disabled {
+  cursor: wait;
+  opacity: 0.5;
+}
+
 .helpLabel {
   margin: 24px 0 0;
   font-size: 13px;
diff --git a/src/pages/LinkUploadPage/LinkUploadPage.test.tsx b/src/pages/LinkUploadPage/LinkUploadPage.test.tsx
index c4c160c..140d7a4 100644
--- a/src/pages/LinkUploadPage/LinkUploadPage.test.tsx
+++ b/src/pages/LinkUploadPage/LinkUploadPage.test.tsx
@@ -28,7 +28,8 @@ beforeEach(() => {
       return Promise.resolve(jsonResponse({ response_id: 'R-1', received_at: '2026-08-04T00:00:00Z' }, 201))
     }
     return Promise.resolve(jsonResponse({
-      guidance: '여권 사본을 제출해 주세요.', due_date: '2026-08-10',
+      guidance: '여권 사본을 제출해 주세요.', language: 'ko', due_date: '2026-08-10',
+      requested_document_types: ['PASSPORT_COPY'],
       allowed_responses: ['QUESTION', 'NOT_UNDERSTOOD', 'DIFFICULT', 'DOCUMENT_SUBMITTED'],
     }))
   }))
@@ -42,7 +43,7 @@ describe('LinkUploadPage', () => {
     renderPage()
     const file = new File(['passport'], 'passport_photo.jpg', { type: 'image/jpeg' })
 
-    await user.upload(await screen.findByLabelText('제출할 파일 선택'), file)
+    await user.upload(await screen.findByLabelText('여권 사본 제출할 파일 선택'), file)
 
     expect(screen.getByText('passport_photo.jpg')).toBeInTheDocument()
     expect(screen.getByText(/제출 전/)).toBeInTheDocument()
@@ -54,8 +55,8 @@ describe('LinkUploadPage', () => {
     renderPage()
     const file = new File(['passport'], 'passport_photo.jpg', { type: 'image/jpeg' })
 
-    await user.upload(await screen.findByLabelText('제출할 파일 선택'), file)
-    await user.click(screen.getByRole('button', { name: '삭제' }))
+    await user.upload(await screen.findByLabelText('여권 사본 제출할 파일 선택'), file)
+    await user.click(screen.getByRole('button', { name: '제거' }))
 
     expect(screen.queryByText('passport_photo.jpg')).not.toBeInTheDocument()
   })
@@ -65,27 +66,131 @@ describe('LinkUploadPage', () => {
     renderPage()
     const file = new File(['script'], 'worker.exe', { type: 'application/octet-stream' })
 
-    await user.upload(await screen.findByLabelText('제출할 파일 선택'), file)
+    await user.upload(await screen.findByLabelText('여권 사본 제출할 파일 선택'), file)
 
-    expect(screen.getByRole('alert')).toHaveTextContent('JPG, PNG, PDF 파일만 선택할 수 있습니다.')
+    expect(screen.getByRole('alert')).toHaveTextContent('JPG, PNG, WEBP, PDF 파일만 선택할 수 있습니다.')
     expect(screen.queryByText('worker.exe')).not.toBeInTheDocument()
   })
 
   it('uploads the selected file and submits the upload id as a worker response', async () => {
     const user = userEvent.setup()
     renderPage()
-    await screen.findByRole('heading', { name: '사진 또는 파일을 추가해 주세요' })
+    await screen.findByRole('heading', { name: '요청받은 서류를 추가해 주세요' })
     const file = new File(['passport'], 'passport_photo.jpg', { type: 'image/jpeg' })
 
-    await user.upload(await screen.findByLabelText('제출할 파일 선택'), file)
+    await user.upload(await screen.findByLabelText('여권 사본 제출할 파일 선택'), file)
     await user.click(screen.getByRole('button', { name: '서류 제출' }))
 
     expect(await screen.findByText('서류를 제출했습니다')).toBeInTheDocument()
     const calls = vi.mocked(fetch).mock.calls
     expect(calls.some(([url]) => String(url).endsWith('/documents'))).toBe(true)
+    const uploadCall = calls.find(([url]) => String(url).endsWith('/documents'))
+    expect((uploadCall?.[1]?.body as FormData).get('documentType')).toBe('PASSPORT_COPY')
     const responseCall = calls.find(([url]) => String(url).endsWith('/responses'))
     expect(JSON.parse(responseCall?.[1]?.body as string)).toMatchObject({
       response_type: 'DOCUMENT_SUBMITTED', upload_ids: ['U-1'],
     })
   })
+
+  it('uploads every requested document with its type before submitting one response', async () => {
+    const user = userEvent.setup()
+    let uploadCount = 0
+    vi.mocked(fetch).mockImplementation((input) => {
+      const url = String(input)
+      if (url.endsWith('/documents')) {
+        uploadCount += 1
+        return Promise.resolve(jsonResponse({
+          upload_id: `U-${uploadCount}`,
+          file_name: `document-${uploadCount}.jpg`,
+          size: 8,
+          expires_at: '2026-08-07T00:00:00Z',
+        }, 201))
+      }
+      if (url.endsWith('/responses')) {
+        return Promise.resolve(jsonResponse({
+          response_id: 'R-1',
+          received_at: '2026-08-04T00:00:00Z',
+        }, 201))
+      }
+      return Promise.resolve(jsonResponse({
+        guidance: '여권과 계약서를 제출해 주세요.',
+        language: 'ko',
+        due_date: '2026-08-10',
+        requested_document_types: ['PASSPORT_COPY', 'CONTRACT'],
+        allowed_responses: ['DOCUMENT_SUBMITTED'],
+      }))
+    })
+    renderPage()
+
+    await user.upload(
+      await screen.findByLabelText('여권 사본 제출할 파일 선택'),
+      new File(['passport'], 'passport.jpg', { type: 'image/jpeg' }),
+    )
+    await user.upload(
+      screen.getByLabelText('근로계약서 제출할 파일 선택'),
+      new File(['contract'], 'contract.pdf', { type: 'application/pdf' }),
+    )
+    expect(screen.getByText('2 / 2')).toBeInTheDocument()
+    await user.click(screen.getByRole('button', { name: '서류 제출' }))
+
+    expect(await screen.findByText('서류를 제출했습니다')).toBeInTheDocument()
+    const calls = vi.mocked(fetch).mock.calls
+    const uploadTypes = calls
+      .filter(([url]) => String(url).endsWith('/documents'))
+      .map(([, init]) => (init?.body as FormData).get('documentType'))
+    expect(uploadTypes).toEqual(['PASSPORT_COPY', 'CONTRACT'])
+    const responseCall = calls.find(([url]) => String(url).endsWith('/responses'))
+    expect(JSON.parse(String(responseCall?.[1]?.body))).toMatchObject({
+      response_type: 'DOCUMENT_SUBMITTED',
+      upload_ids: ['U-1', 'U-2'],
+    })
+  })
+
+  it('reuses uploaded files and the response idempotency key after a network retry', async () => {
+    const user = userEvent.setup()
+    let responseAttempts = 0
+    vi.mocked(fetch).mockImplementation((input) => {
+      const url = String(input)
+      if (url.endsWith('/documents')) {
+        return Promise.resolve(jsonResponse({
+          upload_id: 'U-1',
+          file_name: 'passport.jpg',
+          size: 8,
+          expires_at: '2026-08-07T00:00:00Z',
+        }, 201))
+      }
+      if (url.endsWith('/responses')) {
+        responseAttempts += 1
+        if (responseAttempts === 1) return Promise.reject(new TypeError('network failed'))
+        return Promise.resolve(jsonResponse({
+          response_id: 'R-1',
+          received_at: '2026-08-04T00:00:00Z',
+        }, 201))
+      }
+      return Promise.resolve(jsonResponse({
+        guidance: '여권을 제출해 주세요.',
+        language: 'ko',
+        due_date: '2026-08-10',
+        requested_document_types: ['PASSPORT_COPY'],
+        allowed_responses: ['DOCUMENT_SUBMITTED'],
+      }))
+    })
+    renderPage()
+    await user.upload(
+      await screen.findByLabelText('여권 사본 제출할 파일 선택'),
+      new File(['passport'], 'passport.jpg', { type: 'image/jpeg' }),
+    )
+
+    await user.click(screen.getByRole('button', { name: '서류 제출' }))
+    expect(await screen.findByRole('alert')).toHaveTextContent('네트워크 상태를 확인')
+    await user.click(screen.getByRole('button', { name: '서류 제출' }))
+
+    expect(await screen.findByText('서류를 제출했습니다')).toBeInTheDocument()
+    const calls = vi.mocked(fetch).mock.calls
+    expect(calls.filter(([url]) => String(url).endsWith('/documents'))).toHaveLength(1)
+    const responseCalls = calls.filter(([url]) => String(url).endsWith('/responses'))
+    expect(responseCalls).toHaveLength(2)
+    const responseBodies = responseCalls.map(([, init]) => JSON.parse(String(init?.body)))
+    expect(responseBodies[0].idempotency_key).toBe(responseBodies[1].idempotency_key)
+  })
 })
diff --git a/src/pages/LinkUploadPage/LinkUploadPage.tsx b/src/pages/LinkUploadPage/LinkUploadPage.tsx
index db17880..bf0554f 100644
--- a/src/pages/LinkUploadPage/LinkUploadPage.tsx
+++ b/src/pages/LinkUploadPage/LinkUploadPage.tsx
@@ -1,5 +1,6 @@
 import { useCallback, useEffect, useRef, useState, type ChangeEvent } from 'react'
 import { useNavigate, useParams } from 'react-router-dom'
+import type { DocumentType } from '../../api/documents'
 import { ApiError, getErrorMessage } from '../../api/errors'
 import {
   fetchWorkerLink,
@@ -11,11 +12,12 @@ import {
 import { MobileShell } from '../../components/mobile/MobileShell'
 import { EmptyState } from '../../components/ui/EmptyState/EmptyState'
 import { useApiQuery } from '../../hooks/useApiQuery'
+import { DOCUMENT_TYPE_LABEL } from '../../utils/documentLabels'
 import styles from './LinkUploadPage.module.css'
 import { HELP_LINKS } from './linkUploadData'
 
-const MAX_FILE_SIZE = 10 * 1024 * 1024
-const ACCEPTED_FILE_TYPES = ['image/jpeg', 'image/png', 'application/pdf']
+const MAX_FILE_SIZE = 20 * 1024 * 1024
+const ACCEPTED_FILE_TYPES = ['image/jpeg', 'image/png', 'image/webp', 'application/pdf']
 
 function formatFileSize(bytes: number) {
   if (bytes < 1024 * 1024) return `${Math.max(1, Math.round(bytes / 1024))}KB`
@@ -25,12 +27,16 @@ function formatFileSize(bytes: number) {
 export function LinkUploadPage() {
   const { token } = useParams()
   const navigate = useNavigate()
-  const fileInputRef = useRef<HTMLInputElement>(null)
-  const [file, setFile] = useState<File | null>(null)
-  const [fileError, setFileError] = useState<string | null>(null)
+  const fileInputRefs = useRef<Partial<Record<DocumentType, HTMLInputElement>>>({})
+  const uploadRequestIds = useRef<Partial<Record<DocumentType, string>>>({})
+  const responseRequestId = useRef<string | null>(null)
+  const [files, setFiles] = useState<Partial<Record<DocumentType, File>>>({})
+  const [fileErrors, setFileErrors] = useState<Partial<Record<DocumentType, string>>>({})
+  const [uploadedIds, setUploadedIds] = useState<Partial<Record<DocumentType, string>>>({})
   const [submitting, setSubmitting] = useState(false)
   const [submission, setSubmission] = useState<WorkerResponseSubmitResponse | null>(null)
   const [responseMessage, setResponseMessage] = useState<string | null>(null)
+  const [submissionError, setSubmissionError] = useState<string | null>(null)
   const fetcher = useCallback(
     () => (token ? fetchWorkerLink(token) : Promise.reject(new Error('missing token'))),
     [token],
@@ -43,42 +49,77 @@ export function LinkUploadPage() {
     }
   }, [error, navigate, status, token])
 
-  function handleFileChange(event: ChangeEvent<HTMLInputElement>) {
+  function handleFileChange(documentType: DocumentType, event: ChangeEvent<HTMLInputElement>) {
     const selected = event.target.files?.[0] ?? null
-    setFileError(null)
+    setFileErrors((current) => ({ ...current, [documentType]: undefined }))
+    setSubmissionError(null)
     if (!selected) return
     if (!ACCEPTED_FILE_TYPES.includes(selected.type)) {
-      setFile(null)
-      setFileError('JPG, PNG, PDF 파일만 선택할 수 있습니다.')
+      setFiles((current) => ({ ...current, [documentType]: undefined }))
+      setFileErrors((current) => ({
+        ...current,
+        [documentType]: 'JPG, PNG, WEBP, PDF 파일만 선택할 수 있습니다.',
+      }))
       event.target.value = ''
       return
     }
     if (selected.size > MAX_FILE_SIZE) {
-      setFile(null)
-      setFileError('파일 크기는 10MB 이하여야 합니다.')
+      setFiles((current) => ({ ...current, [documentType]: undefined }))
+      setFileErrors((current) => ({
+        ...current,
+        [documentType]: '파일 크기는 20MB 이하여야 합니다.',
+      }))
       event.target.value = ''
       return
     }
-    setFile(selected)
+    setFiles((current) => ({ ...current, [documentType]: selected }))
+    setUploadedIds((current) => ({ ...current, [documentType]: undefined }))
+    delete uploadRequestIds.current[documentType]
+    responseRequestId.current = null
   }
 
-  function handleRemoveFile() {
-    setFile(null)
-    setFileError(null)
-    if (fileInputRef.current) fileInputRef.current.value = ''
+  function handleRemoveFile(documentType: DocumentType) {
+    setFiles((current) => ({ ...current, [documentType]: undefined }))
+    setFileErrors((current) => ({ ...current, [documentType]: undefined }))
+    setUploadedIds((current) => ({ ...current, [documentType]: undefined }))
+    delete uploadRequestIds.current[documentType]
+    responseRequestId.current = null
+    const input = fileInputRefs.current[documentType]
+    if (input) input.value = ''
   }
 
   async function handleSubmit() {
-    if (!token || !file || submitting) return
+    if (!token || !data || submitting) return
+    const requestedTypes = [...new Set(data.requested_document_types)]
+    if (requestedTypes.length === 0 || requestedTypes.some((type) => !files[type])) {
+      setSubmissionError('요청받은 서류의 파일을 모두 선택해 주세요.')
+      return
+    }
     setSubmitting(true)
-    setFileError(null)
-    const uploadRequestId = crypto.randomUUID()
+    setSubmissionError(null)
     try {
-      const upload = await uploadWorkerLinkDocument(token, file, uploadRequestId)
+      const nextUploadedIds = { ...uploadedIds }
+      for (const documentType of requestedTypes) {
+        if (nextUploadedIds[documentType]) continue
+        const file = files[documentType]
+        if (!file) throw new Error('missing selected file')
+        const requestId = uploadRequestIds.current[documentType] ?? crypto.randomUUID()
+        uploadRequestIds.current[documentType] = requestId
+        const upload = await uploadWorkerLinkDocument(
+          token,
+          file,
+          requestId,
+          documentType,
+        )
+        nextUploadedIds[documentType] = upload.upload_id
+        setUploadedIds({ ...nextUploadedIds })
+      }
+      const idempotencyKey = responseRequestId.current ?? crypto.randomUUID()
+      responseRequestId.current = idempotencyKey
       const result = await submitWorkerResponse(token, {
         response_type: 'DOCUMENT_SUBMITTED',
-        upload_ids: [upload.upload_id],
-        idempotency_key: crypto.randomUUID(),
+        upload_ids: requestedTypes.map((type) => nextUploadedIds[type]!),
+        idempotency_key: idempotencyKey,
       })
       setSubmission(result)
     } catch (caught) {
@@ -86,7 +127,7 @@ export function LinkUploadPage() {
         navigate(`/worker-portal/${encodeURIComponent(token)}/expired`, { replace: true })
         return
       }
-      setFileError(
+      setSubmissionError(
         caught instanceof ApiError ? getErrorMessage(caught) : '파일을 제출하지 못했습니다.',
       )
     } finally {
@@ -97,7 +138,7 @@ export function LinkUploadPage() {
   async function handleHelpResponse(responseType: WorkerResponseType, successMessage: string) {
     if (!token || submitting) return
     setSubmitting(true)
-    setFileError(null)
+    setSubmissionError(null)
     try {
       await submitWorkerResponse(token, {
         response_type: responseType,
@@ -105,7 +146,11 @@ export function LinkUploadPage() {
       })
       setResponseMessage(successMessage)
     } catch (caught) {
-      setFileError(
+      if (caught instanceof ApiError && caught.status === 410) {
+        navigate(`/worker-portal/${encodeURIComponent(token)}/expired`, { replace: true })
+        return
+      }
+      setSubmissionError(
         caught instanceof ApiError ? getErrorMessage(caught) : '응답을 보내지 못했습니다.',
       )
     } finally {
@@ -138,13 +183,19 @@ export function LinkUploadPage() {
   }
 
   if (status === 'error' || !data) {
+    const contentNotReady =
+      error instanceof ApiError && error.code === 'WORKER_LINK_CONTENT_NOT_READY'
     return (
       <MobileShell title="서류 제출" onBack={() => navigate(-1)}>
         <EmptyState
           kind="error"
-          title="제출 링크를 확인하지 못했습니다"
+          title={contentNotReady ? '요청 내용을 준비하고 있습니다' : '제출 링크를 확인하지 못했습니다'}
           body={
-            error instanceof ApiError ? getErrorMessage(error) : '네트워크 상태를 확인해 주세요.'
+            contentNotReady
+              ? '회사 담당자가 안내문을 준비 중입니다. 잠시 후 같은 링크에서 다시 확인해 주세요.'
+              : error instanceof ApiError
+                ? getErrorMessage(error)
+                : '네트워크 상태를 확인해 주세요.'
           }
           actionLabel="다시 시도"
           onAction={refetch}
@@ -167,6 +218,10 @@ export function LinkUploadPage() {
   }
 
   const canSubmitDocument = data.allowed_responses.includes('DOCUMENT_SUBMITTED')
+  const requestedTypes = [...new Set(data.requested_document_types)]
+  const selectedCount = requestedTypes.filter((type) => files[type]).length
+  const allRequestedFilesSelected =
+    requestedTypes.length > 0 && selectedCount === requestedTypes.length
   const helpResponses: Array<{ label: string; type: WorkerResponseType; message: string }> = [
     { label: HELP_LINKS[0], type: 'QUESTION', message: '담당자에게 질문 의사를 전했습니다.' },
     {
@@ -182,54 +237,87 @@ export function LinkUploadPage() {
   ]
 
   return (
-    <MobileShell title="요청 서류 제출" onBack={() => navigate(-1)} right={<span>1 / 1</span>}>
+    <MobileShell
+      title="요청 서류 제출"
+      onBack={() => navigate(-1)}
+      right={<span>{selectedCount} / {requestedTypes.length}</span>}
+    >
       <h1 className={styles.headline}>
-        사진 또는 파일을
+        요청받은 서류를
         <br />
         추가해 주세요
       </h1>
       <p className={styles.subtext}>
-        여권 사진면 전체가 보이고 글자가 흐리지 않은지 확인해 주세요.
+        각 서류의 글자와 사진이 선명하게 보이는지 확인해 주세요.
       </p>
 
-      <button
-        type="button"
-        className={styles.dropzone}
-        aria-label="파일 또는 사진 선택"
-        onClick={() => fileInputRef.current?.click()}
-      >
-        <p className={styles.dropzonePlus}>＋</p>
-        <p className={styles.dropzoneLabel}>파일 또는 사진 선택</p>
-        <p className={styles.dropzoneHint}>JPG, PNG, PDF · 최대 10MB</p>
-      </button>
-      <input
-        ref={fileInputRef}
-        className={styles.fileInput}
-        type="file"
-        accept=".jpg,.jpeg,.png,.pdf,image/jpeg,image/png,application/pdf"
-        aria-label="제출할 파일 선택"
-        onChange={handleFileChange}
-      />
+      <div className={styles.requestList}>
+        {requestedTypes.map((documentType) => {
+          const file = files[documentType]
+          const documentLabel = DOCUMENT_TYPE_LABEL[documentType]
+          return (
+            <section key={documentType} className={styles.requestCard}>
+              <div className={styles.requestCardHeader}>
+                <h2 className={styles.requestTitle}>{documentLabel}</h2>
+                <span>{file ? '선택 완료' : '파일 필요'}</span>
+              </div>
+              <button
+                type="button"
+                className={styles.dropzone}
+                aria-label={`${documentLabel} 파일 또는 사진 선택`}
+                disabled={submitting}
+                onClick={() => fileInputRefs.current[documentType]?.click()}
+              >
+                <p className={styles.dropzonePlus}>{file ? '↻' : '＋'}</p>
+                <p className={styles.dropzoneLabel}>{file ? '다른 파일 선택' : '파일 또는 사진 선택'}</p>
+                <p className={styles.dropzoneHint}>JPG, PNG, WEBP, PDF · 최대 20MB</p>
+              </button>
+              <input
+                ref={(element) => {
+                  if (element) fileInputRefs.current[documentType] = element
+                }}
+                className={styles.fileInput}
+                type="file"
+                accept=".jpg,.jpeg,.png,.webp,.pdf,image/jpeg,image/png,image/webp,application/pdf"
+                aria-label={`${documentLabel} 제출할 파일 선택`}
+                disabled={submitting}
+                onChange={(event) => handleFileChange(documentType, event)}
+              />
+
+              {fileErrors[documentType] && (
+                <p className={styles.fileError} role="alert">
+                  {fileErrors[documentType]}
+                </p>
+              )}
+
+              {file && (
+                <div className={styles.selectedFile}>
+                  <div>
+                    <p className={styles.fileName}>{file.name}</p>
+                    <p className={styles.fileMeta}>{formatFileSize(file.size)} · 제출 전 확인</p>
+                  </div>
+                  <button
+                    type="button"
+                    className={styles.removeFile}
+                    disabled={submitting}
+                    onClick={() => handleRemoveFile(documentType)}
+                  >
+                    제거
+                  </button>
+                </div>
+              )}
+            </section>
+          )
+        })}
+      </div>
 
-      {fileError && (
+      {submissionError && (
         <p className={styles.fileError} role="alert">
-          {fileError}
+          {submissionError}
         </p>
       )}
       {responseMessage && <p className={styles.responseNotice}>{responseMessage}</p>}
 
-      {file && (
-        <div className={styles.selectedFile}>
-          <div>
-            <p className={styles.fileName}>{file.name}</p>
-            <p className={styles.fileMeta}>{formatFileSize(file.size)} · 제출 전 확인</p>
-          </div>
-          <button type="button" className={styles.removeFile} onClick={handleRemoveFile}>
-            삭제
-          </button>
-        </div>
-      )}
-
       <p className={styles.helpLabel}>제출이 어렵다면</p>
       <div className={styles.helpLinks}>
         {helpResponses.map((response, index) => (
@@ -249,7 +337,7 @@ export function LinkUploadPage() {
       <button
         type="button"
         className={styles.submit}
-        disabled={!file || !canSubmitDocument || submitting}
+        disabled={!allRequestedFilesSelected || !canSubmitDocument || submitting}
         onClick={handleSubmit}
       >
         {submitting ? '제출 중…' : '서류 제출'}