diff --git a/core/http/react-ui/e2e/forking-chat.spec.js b/core/http/react-ui/e2e/forking-chat.spec.js
index c1625de7e..6cb0dac34 100644
--- a/core/http/react-ui/e2e/forking-chat.spec.js
+++ b/core/http/react-ui/e2e/forking-chat.spec.js
@@ -98,6 +98,53 @@ test('retry regenerates the first answer and drops the later turn', async ({ pag
   expect(contents.join('\n')).not.toContain('first answer')
 })
 
+const FILE_TURNS = [
+  {
+    role: 'user',
+    content: [
+      { type: 'text', text: 'what does the file say' },
+      { type: 'text', text: '\n\n--- File: notes.txt ---\nthe secret is 42\n--- End of notes.txt ---' },
+    ],
+    files: [{ name: 'notes.txt', type: 'file', content: 'the secret is 42' }],
+  },
+  { role: 'assistant', content: 'the file says the secret is 42' },
+  { role: 'user', content: 'anything else' },
+  { role: 'assistant', content: 'nope, that is it' },
+]
+
+test('regenerating a non-last answer in a fork still sends the uploaded file content', async ({ page }) => {
+  await mockModels(page)
+  let sentMessages = null
+  await page.route('**/v1/chat/completions', (route) => {
+    sentMessages = route.request().postDataJSON()?.messages || []
+    const sse =
+      `data: ${JSON.stringify({ choices: [{ delta: { content: 'REGENERATED file answer' } }] })}\n\n` +
+      `data: ${JSON.stringify({ choices: [{ delta: {}, finish_reason: 'stop' }], usage: { prompt_tokens: 1, completion_tokens: 1, total_tokens: 2 } })}\n\n` +
+      `data: [DONE]\n\n`
+    route.fulfill({ status: 200, contentType: 'text/event-stream', body: sse })
+  })
+  await seedChat(page, FILE_TURNS)
+  await page.goto('/app/chat')
+
+  // Fork after the second turn, then regenerate the FIRST (now non-last) answer.
+  const secondAssistant = page.locator('.chat-message-assistant').nth(1)
+  await secondAssistant.hover()
+  await secondAssistant.getByTitle('Branch from here').click()
+  await expect(page.locator('.chat-header-title')).toHaveText('Seeded Chat (fork)')
+
+  const firstAssistant = page.locator('.chat-message-assistant').first()
+  await firstAssistant.hover()
+  await firstAssistant.getByTitle('Regenerate').click()
+
+  await expect(page.locator('.chat-message-assistant')).toContainText(['REGENERATED file answer'])
+
+  // The outbound payload for the regenerated turn must still carry the file text.
+  const contents = (sentMessages || []).map(m =>
+    typeof m.content === 'string' ? m.content : JSON.stringify(m.content)
+  )
+  expect(contents.join('\n')).toContain('the secret is 42')
+})
+
 test('copy chat puts the whole conversation on the clipboard', async ({ page, context }) => {
   await context.grantPermissions(['clipboard-read', 'clipboard-write'])
   await mockModels(page)
diff --git a/core/http/react-ui/src/hooks/useChat.js b/core/http/react-ui/src/hooks/useChat.js
index ee00ccec1..2bcf955ce 100644
--- a/core/http/react-ui/src/hooks/useChat.js
+++ b/core/http/react-ui/src/hooks/useChat.js
@@ -218,8 +218,15 @@ export function useChat(initialModel = '') {
 
     // Build user message content
     let messageContent
-    const userFiles = []
-    if (files.length > 0) {
+    let userFiles = []
+    if (options.prebuiltContent) {
+      // Caller (e.g. regenerate) already has the fully-assembled content from
+      // the original send — reuse it verbatim instead of rebuilding from
+      // display-only file metadata, which doesn't carry the base64/text
+      // payload needed to re-embed attachments.
+      messageContent = content
+      userFiles = files
+    } else if (files.length > 0) {
       messageContent = [{ type: 'text', text: content }]
       for (const file of files) {
         if (file.type?.startsWith('image/')) {
diff --git a/core/http/react-ui/src/pages/Chat.jsx b/core/http/react-ui/src/pages/Chat.jsx
index f75b7996f..df867ef43 100644
--- a/core/http/react-ui/src/pages/Chat.jsx
+++ b/core/http/react-ui/src/pages/Chat.jsx
@@ -809,9 +809,11 @@ export default function Chat() {
       if (history[i].role === 'user') { userIdx = i; break }
     }
     if (userIdx === -1) return
-    const userMsg = typeof history[userIdx].content === 'string'
-      ? history[userIdx].content
-      : history[userIdx].content?.[0]?.text || ''
+    // Reuse the original message's content verbatim (not re-extracted text):
+    // it already has any file text / image_url / audio_url / video_url parts
+    // embedded from when it was first sent, which display-only file metadata
+    // can't reconstruct.
+    const userContent = history[userIdx].content
     const userFiles = history[userIdx].files || []
     // Drop the user turn and everything after it; sendMessage re-appends it.
     // Thread the truncated history through explicitly: updateChatSettings only
@@ -819,7 +821,7 @@ export default function Chat() {
     // the stale pre-truncation history for the outbound API payload.
     const baseHistory = history.slice(0, userIdx)
     updateChatSettings(activeChat.id, { history: baseHistory })
-    await sendMessage(userMsg, userFiles, { baseHistory })
+    await sendMessage(userContent, userFiles, { baseHistory, prebuiltContent: true })
   }, [activeChat, isStreaming, sendMessage, updateChatSettings])
 
   const handleKeyDown = (e) => {