fix(mobile): send iPhone library photos as JPEG named .jpg, not HEIC named .png (#36989)

* fix(mobile): save iPhone library photos as JPEG named by their bytes

The iOS photo picker handed back the asset's HEIC bytes as-is, and the host
named every pasted image .png, so agents read a HEIC file as a PNG and failed.
Ask the picker for the compatible representation (JPEG), and name pasted
images by their signature so the extension always matches the bytes.

* fix(mobile): keep unknown pasted bytes on the .png name

A .heic name falls outside the shared image MIME table, so chat previews
and agent prompts would drop the image. The picker now sends JPEG, so
leave HEIC detection out.

* refactor(mobile): keep the pasted image extension list module-private

mobile/src/platform/mobile-picked-file-name.ts

@@ -22,7 +22,7 @@ export function mobilePickedFileFallbackName(mime: string, index: number): strin
   return extension ? `attachment-${index}.${extension}` : `attachment-${index}`
 }
 
-// Images keep the host's orca-paste-*.png name, which transcript readers recognize as a pasted image.
+// Images take the host's orca-paste-* name, which transcript readers recognize as a pasted image.
 export function isPickedImageMime(mime: string | null | undefined): boolean {
   return mime?.trim().toLowerCase().startsWith('image/') ?? false
 }

mobile/src/platform/native-media-device.test.ts

@@ -15,6 +15,7 @@ const expo = vi.hoisted(() => ({
 vi.mock('expo-clipboard', () => ({ getImageAsync: expo.getImageAsync }))
 vi.mock('expo-document-picker', () => ({ getDocumentAsync: expo.getDocumentAsync }))
 vi.mock('expo-image-picker', () => ({
+  UIImagePickerPreferredAssetRepresentationMode: { Compatible: 'compatible' },
   launchImageLibraryAsync: expo.launchImageLibraryAsync,
   requestMediaLibraryPermissionsAsync: expo.requestMediaLibraryPermissionsAsync
 }))
@@ -92,7 +93,9 @@ describe('how the pickers are launched', () => {
       expect.objectContaining({
         mediaTypes: ['images'],
         base64: false,
-        allowsMultipleSelection: false
+        allowsMultipleSelection: false,
+        // Agents can't read the HEIC iOS hands back by default.
+        preferredAssetRepresentationMode: 'compatible'
       })
     )
     // Omit selectionLimit for single picks; zero means unlimited.

mobile/src/platform/native-media-device.ts

@@ -51,7 +51,10 @@ export function nativeMediaDeviceDeps(registry: MediaHandleRegistry): NativeMedi
         base64: false,
         allowsMultipleSelection: multiple,
         ...(multiple ? { selectionLimit: limit, orderedSelection: true } : {}),
-        quality: 1
+        quality: 1,
+        // iOS otherwise hands back HEIC as-is, which agents can't read; Compatible gives JPEG.
+        preferredAssetRepresentationMode:
+          ImagePicker.UIImagePickerPreferredAssetRepresentationMode.Compatible
       }),
     // DocumentPicker has no selection cap; enforce remaining room again before staging and minting.
     launchFiles: ({ multiple }) =>

mobile/src/platform/use-native-device-verbs.test.tsx

@@ -44,6 +44,7 @@ vi.mock('expo-keep-awake', () => ({
   }
 }))
 vi.mock('expo-image-picker', () => ({
+  UIImagePickerPreferredAssetRepresentationMode: { Compatible: 'compatible' },
   launchImageLibraryAsync: device.picker.launchImageLibraryAsync
 }))
 vi.mock('expo-file-system', () => ({

mobile/src/session/mobile-image-source-picker.test.ts

@@ -2,6 +2,7 @@ import { afterEach, describe, expect, it, vi } from 'vitest'
 import { CLIPBOARD_IMAGE_MAX_SOURCE_BYTES } from '../../../src/shared/clipboard-image'
 
 vi.mock('expo-image-picker', () => ({
+  UIImagePickerPreferredAssetRepresentationMode: { Compatible: 'compatible' },
   requestMediaLibraryPermissionsAsync: vi.fn(),
   launchImageLibraryAsync: vi.fn()
 }))
@@ -78,7 +79,9 @@ describe('pickMobileImage', () => {
       base64: Buffer.from(bytes).toString('base64'),
       uri: 'file:///x.jpg'
     })
-    expect(launchLibrary).toHaveBeenCalledWith(expect.objectContaining({ base64: false }))
+    expect(launchLibrary).toHaveBeenCalledWith(
+      expect.objectContaining({ base64: false, preferredAssetRepresentationMode: 'compatible' })
+    )
     expect(fetchSpy).not.toHaveBeenCalled()
     expect(file.close).toHaveBeenCalledTimes(1)
   })

mobile/src/session/mobile-image-source-picker.ts

@@ -90,7 +90,10 @@ async function* pickFromLibrary(
     base64: false,
     allowsMultipleSelection: multiple,
     ...(multiple ? { selectionLimit: 0, orderedSelection: true } : {}),
-    quality: 1
+    quality: 1,
+    // iOS otherwise hands back HEIC as-is, which agents can't read; Compatible gives JPEG.
+    preferredAssetRepresentationMode:
+      ImagePicker.UIImagePickerPreferredAssetRepresentationMode.Compatible
   })
   if (result.canceled) {
     return

src/main/native-chat/transcript-line-decoders-grok.ts

@@ -6,6 +6,7 @@ import {
   timestampMs
 } from '../ai-vault/session-scanner-values'
 import { claudeContentBlocks, toolResultOutput } from './transcript-record-blocks'
+import { AGENT_SESSION_PASTED_IMAGE_SUFFIX_SOURCE } from '../../shared/agent-session-attachments'
 
 export function decodeGrokTranscriptLine(
   line: string,
@@ -209,11 +210,16 @@ function normalizeGrokUserQueryBlock(block: NativeChatBlock): NativeChatBlock[]
   ]
 }
 
+const GROK_PASTED_IMAGE_QUERY = new RegExp(
+  String.raw`^((?:[a-z]:[\\/]|\/|[\\/]{2}[^\\/\r\n]+[\\/][^\\/\r\n]+[\\/])(?:.*?[\\/])?orca-paste-[^\\/\r\n]+?` +
+    AGENT_SESSION_PASTED_IMAGE_SUFFIX_SOURCE +
+    String.raw`)([\s\S]*)$`,
+  'i'
+)
+
 function splitGrokPastedImageQuery(text: string): { path: string; query: string } | null {
   // Grok 0.2.93 concatenates clipboard temp paths with prompts; recover the attachment separately.
-  const match = text.match(
-    /^((?:[a-z]:[\\/]|\/|[\\/]{2}[^\\/\r\n]+[\\/][^\\/\r\n]+[\\/])(?:.*?[\\/])?orca-paste-[^\\/\r\n]+?\.png)([\s\S]*)$/i
-  )
+  const match = text.match(GROK_PASTED_IMAGE_QUERY)
   if (!match?.[1]) {
     return null
   }

src/main/native-chat/transcript-line-decoders.grok.test.ts

@@ -36,6 +36,7 @@ describe('decodeGrokTranscriptLine', () => {
   it.each([
     'C:\\Users\\me\\AppData\\Local\\Temp\\orca-paste-1783675302563-2207c073-535f-4b83-a181-61127c8bbd68.png',
     '/tmp/orca-paste-1783675302563-2207c073-535f-4b83-a181-61127c8bbd68.png',
+    '/tmp/orca-paste-1783675302563-2207c073-535f-4b83-a181-61127c8bbd68.jpg',
     'C:\\orca-paste-1783675302563-2207c073-535f-4b83-a181-61127c8bbd68.png',
     '/orca-paste-1783675302563-2207c073-535f-4b83-a181-61127c8bbd68.png',
     '\\\\server\\temp\\orca-paste-1783675302563-2207c073-535f-4b83-a181-61127c8bbd68.png'

src/main/window/clipboard-image-temp-file.test.ts

@@ -32,6 +32,13 @@ describe('saveClipboardImageBufferAsTempFile', () => {
     expect(writeFileMock).toHaveBeenCalledWith(savedPath, Buffer.from([1, 2, 3]))
   })
 
+  it('names a JPEG phone pick by its bytes, not as a .png', async () => {
+    const jpeg = Buffer.from([0xff, 0xd8, 0xff, 0xe0, 0, 0x10, 0x4a, 0x46, 0x49, 0x46, 0, 1])
+    const savedPath = await saveClipboardImageBufferAsTempFile(jpeg)
+
+    expect(basename(savedPath)).toMatch(/^orca-paste-\d+-uuid-1\.jpg$/)
+  })
+
   it('writes a terminal-backed composer paste into the never-swept paste folder', async () => {
     const savedPath = await saveClipboardImageBufferAsTempFile(Buffer.from([1, 2, 3]), {
       forNativeChatDraft: true

src/main/window/clipboard-image-temp-file.ts

@@ -10,11 +10,12 @@ import {
   sanitizeAgentSessionAttachmentName,
   type AgentSessionAttachmentClipboardTarget
 } from '../../shared/agent-session-attachments'
+import { detectImageFileSignature } from '../image-file-signature'
 import { nativeChatPasteFolder } from './native-chat-paste-files'
 
 export type SaveClipboardImageAsTempFileArgs = {
   connectionId?: string | null
-  /** A phone-picked file's own name; without it the paste is saved as a .png. */
+  /** A phone-picked file's own name; without it the paste is named by its image bytes. */
   fileName?: string
   runtimeEnvironmentId?: string | null
   /** With `runtimeEnvironmentId`: store the image as an attachment of this structured chat. */
@@ -49,7 +50,15 @@ export async function saveClipboardImageBufferAsTempFile(
   // A picked file keeps its own name, so the paste gets a folder to stay unique.
   const tempPath = args?.fileName
     ? path.join(folder, `orca-paste-${randomUUID()}`, shellInertFileName(args.fileName))
-    : path.join(folder, agentSessionPastedImageName(Date.now(), randomUUID()))
+    : path.join(
+        folder,
+        // Phone library picks are often JPEG; agents trust the extension over the bytes.
+        agentSessionPastedImageName(
+          Date.now(),
+          randomUUID(),
+          detectImageFileSignature(buffer)?.extension
+        )
+      )
   if (args?.fileName) {
     await fs.mkdir(path.dirname(tempPath), { recursive: true })
   }

src/shared/agent-session-attachments.ts

@@ -122,9 +122,20 @@ export type AgentSessionAttachmentClipboardTarget = Omit<
   'environmentId'
 >
 
-/** `orca-paste-…png`, the name every pasted image gets, so it reads as "Pasted image". */
-export function agentSessionPastedImageName(now: number, unique: string): string {
-  return `orca-paste-${now}-${unique}.png`
+/** Extensions a pasted image's name can carry; the host picks one from the image's bytes. */
+const AGENT_SESSION_PASTED_IMAGE_EXTENSIONS = ['png', 'jpg', 'gif', 'webp'] as const
+type AgentSessionPastedImageExtension = (typeof AGENT_SESSION_PASTED_IMAGE_EXTENSIONS)[number]
+
+/** Matches the `.png`, `.jpg`… suffix of a pasted image's name. */
+export const AGENT_SESSION_PASTED_IMAGE_SUFFIX_SOURCE = `\\.(?:${AGENT_SESSION_PASTED_IMAGE_EXTENSIONS.join('|')})`
+
+/** `orca-paste-…<ext>`, the name every pasted image gets, so it reads as "Pasted image". */
+export function agentSessionPastedImageName(
+  now: number,
+  unique: string,
+  extension: AgentSessionPastedImageExtension = 'png'
+): string {
+  return `orca-paste-${now}-${unique}.${extension}`
 }
 
 /** `orca-paste-…txt`, the name a long text paste saved as a file gets, so it reads as "Pasted text". */

src/shared/native-chat-image-label.ts

@@ -1,3 +1,4 @@
+import { AGENT_SESSION_PASTED_IMAGE_SUFFIX_SOURCE } from './agent-session-attachments'
 import { getRuntimePathBasename } from './cross-platform-path'
 import type { NativeChatImageRefBlock } from './native-chat/native-chat-types'
 
@@ -11,10 +12,15 @@ export const NATIVE_CHAT_IMAGE_LABEL_ENGLISH: NativeChatImageLabelCopy = {
   imageCount: (count) => `${count} images`
 }
 
+const PASTED_IMAGE_NAME = new RegExp(
+  `^orca-paste-.+${AGENT_SESSION_PASTED_IMAGE_SUFFIX_SOURCE}$`,
+  'i'
+)
+
 /** Use friendly UI labels for Orca clipboard-image temp filenames. */
 export function isNativeChatPastedImagePath(path: string): boolean {
   const base = path.split(/[\\/]/).findLast(Boolean) ?? path
-  return /^orca-paste-.+\.png$/i.test(base)
+  return PASTED_IMAGE_NAME.test(base)
 }
 
 /** What a chat image is called where it is not drawn: its alt text, else its file's name. */