diff --git a/e2e/work-companion-live.playwright.ts b/e2e/work-companion-live.playwright.ts
index a2c7fb6..b3be563 100644
--- a/e2e/work-companion-live.playwright.ts
+++ b/e2e/work-companion-live.playwright.ts
@@ -1,4 +1,5 @@
-import { test, expect, type Page, type APIRequestContext } from '@playwright/test'
+import { test, expect, type Page, type APIRequestContext, type Response } from '@playwright/test'
+import type { Artifact, Message, Part, Run, UploadInfo } from '../src/contracts'
 
 test.skip(!process.env.WORK_COMPANION_LIVE_BROWSER, 'Requires the task-owned backend, SQLite data and MockRunner')
 
@@ -18,25 +19,84 @@ async function openRealConversation(page: Page, request: APIRequestContext) {
   return { project, conversation }
 }
 
-test('real upload/send/reload preserves three actual attachments', async ({ page, request }) => {
+test('real upload/send/reload preserves three actual attachments', async ({ page, request }, testInfo) => {
   const { project, conversation } = await openRealConversation(page, request)
   const errors: string[] = []
   page.on('pageerror', error => errors.push(error.message))
+  const uploadResponses: Response[] = []
+  const uploadPath = `/api/projects/${project.id}/uploads`
+  const observeUpload = (response: Response) => {
+    if (response.request().method() === 'POST' && new URL(response.url()).pathname === uploadPath) uploadResponses.push(response)
+  }
+  page.on('response', observeUpload)
   await page.locator('input[type=file]').first().setInputFiles([
     { name: '会议纪要.txt', mimeType: 'text/plain', buffer: Buffer.from('会议决定：先明确交付日期') },
     { name: '需求说明.txt', mimeType: 'text/plain', buffer: Buffer.from('需求：整理材料并生成摘要') },
     { name: '评审意见.txt', mimeType: 'text/plain', buffer: Buffer.from('评审意见：补充验收标准') },
   ])
   await expect(page.locator('.attach-chip')).toHaveCount(3)
-  const artifacts = await request.get(`/api/projects/${project.id}/artifacts`).then(r => r.json())
+  page.off('response', observeUpload)
+  expect(uploadResponses).toHaveLength(3)
+  const uploads: UploadInfo[] = await Promise.all(uploadResponses.map(async response => {
+    expect(response.ok()).toBe(true)
+    return response.json()
+  }))
+  expect(uploads.map(upload => upload.filename)).toEqual(['会议纪要.txt', '需求说明.txt', '评审意见.txt'])
+  const attachmentIds = uploads.map(upload => upload.artifactId)
+  for (const id of attachmentIds) expect(id).toEqual(expect.stringMatching(/\S+/))
+  expect(new Set(attachmentIds).size).toBe(3)
+  const artifactsResponse = await request.get(`/api/projects/${project.id}/artifacts`)
+  expect(artifactsResponse.ok()).toBe(true)
+  const artifacts: Artifact[] = await artifactsResponse.json()
   expect(artifacts).toHaveLength(3)
-  await page.getByRole('button', { name: '发送', exact: true }).click()
+  expect(artifacts.map(artifact => artifact.id).sort()).toEqual([...attachmentIds].sort())
+  const expectedParts: Part[] = uploads.map(upload => {
+    const artifact = artifacts.find(artifact => artifact.id === upload.artifactId)!
+    expect(artifact.name).toBe(upload.filename)
+    return { type: 'artifact_ref', artifact: { artifactId: artifact.id, name: artifact.name, kind: artifact.kind } }
+  })
+  const messagePath = `/api/conversations/${conversation.id}/messages`
+  const [sendRequest, sendResponse] = await Promise.all([
+    page.waitForRequest(request => request.method() === 'POST' && new URL(request.url()).pathname === messagePath),
+    page.waitForResponse(response => response.request().method() === 'POST' && new URL(response.url()).pathname === messagePath),
+    page.getByRole('button', { name: '发送', exact: true }).click(),
+  ])
+  const sent = sendRequest.postDataJSON()
+  expect(sent.text).toBe('')
+  expect(sent.attachmentIds).toEqual(attachmentIds)
+  expect(sendResponse.ok()).toBe(true)
+  const accepted: { message: Message; run: Run } = await sendResponse.json()
+  expect(accepted.message.role).toBe('user')
+  expect(accepted.message.conversationId).toBe(conversation.id)
+  expect(accepted.message.parts).toEqual(expectedParts)
+  expect(accepted.run.kind).toBe('conversation')
   await expect.poll(async () => {
-    const current = await request.get(`/api/conversations/${conversation.id}`).then(r => r.json())
-    return current.runs.some((run: { kind: string; status: string }) => run.kind === 'conversation' && run.status === 'completed')
+    const response = await request.get(`/api/conversations/${conversation.id}`)
+    expect(response.ok()).toBe(true)
+    const current: { runs: Run[] } = await response.json()
+    return current.runs.some(run => run.id === accepted.run.id && run.kind === 'conversation' && run.status === 'completed')
   }).toBe(true)
+  async function persistedMessage() {
+    const response = await request.get(`/api/conversations/${conversation.id}`)
+    expect(response.ok()).toBe(true)
+    const current: { messages: Message[] } = await response.json()
+    const users = current.messages.filter(message => message.role === 'user')
+    expect(users).toHaveLength(1)
+    expect(users[0].id).toBe(accepted.message.id)
+    expect(users[0].conversationId).toBe(conversation.id)
+    expect(users[0].parts).toEqual(expectedParts)
+    return users[0]
+  }
+  const beforeReload = await persistedMessage()
   await page.reload()
   await expect(page.locator('.chat-title')).toHaveText('真实接口验收')
+  const afterReload = await persistedMessage()
+  expect(afterReload).toEqual(beforeReload)
+  const association = { projectId: project.id, conversationId: conversation.id, runId: accepted.run.id,
+    uploads: uploads.map(({ artifactId, filename }) => ({ artifactId, filename })),
+    sent: { text: sent.text, attachmentIds: sent.attachmentIds }, beforeReload, afterReload }
+  await testInfo.attach('real-material-associations', { body: Buffer.from(JSON.stringify(association, null, 2)), contentType: 'application/json' })
+  console.log('real-material-associations', JSON.stringify(association))
   await page.getByRole('button', { name: '打开文件', exact: true }).click()
   await expect(page.locator('[data-artifact-row]')).toHaveCount(3)
   await page.locator('[data-artifact-row]').first().click()