From cc291dba1dcf62be1dd9473efdcc863073d23c39 Mon Sep 17 00:00:00 2001
From: Brennan Benson <79079362+brennanb2025@users.noreply.github.com>
Date: Thu, 8 Oct 2026 10:30:49 -0700
Subject: [PATCH] Keep picked skills and pending uploads when native chat
 composers close (#26538)

* Preserve native chat skills and uploads when composers close

* Own menu image pastes before saving begins

* Keep paste ownership independent of image presentation

* Show pending pastes so stalled saves can be removed

* Register confirmed image pastes and preserve preview ownership

* Keep clipboard image presence and saving on one source selector

* Describe clipboard image formats in upload routing fixtures
---
 ...ard-agent-session-attachment-paste.test.ts |   6 +-
 .../window/clipboard-image-source.test.ts     |  72 +++++
 src/main/window/clipboard-image-source.ts     |  33 +++
 .../window/clipboard-ipc-handlers.test.ts     | 129 ++++-----
 src/main/window/clipboard-ipc-handlers.ts     |  24 +-
 .../clipboard-runtime-owned-ssh-paste.test.ts |   3 +-
 .../window/clipboard-windows-image-file.ts    |  13 +-
 .../NativeChatComposer.paste-remount.test.tsx | 229 +++++++++++++--
 .../native-chat/NativeChatComposer.tsx        |   1 +
 .../native-chat/NativeChatComposerField.tsx   |   7 +-
 ...ative-chat-composer-draft-addition.test.ts |  41 +++
 .../native-chat-composer-draft-addition.ts    |   5 +-
 .../native-chat-composer-draft-journal.ts     |   1 -
 .../native-chat-composer-draft-store.ts       |   6 +-
 .../native-chat-composer-paste-options.ts     |  23 ++
 ...e-chat-composer-upload-completion.test.tsx | 230 +++++++++++++++
 .../native-chat/native-chat-draft-cache.ts    |   9 +-
 ...tive-chat-pending-attachment-cache.test.ts |  40 +--
 .../native-chat-pending-attachment-cache.ts   |  40 +--
 .../native-chat-prompt-document-text.test.ts  |  66 +++++
 .../native-chat-prompt-document-text.ts       |  59 ++++
 .../native-chat-prompt-document.ts            |  13 +-
 .../native-chat-session-attachment-drop.ts    |   8 +-
 ...-native-chat-composer-attachments.test.tsx |  40 ++-
 .../use-native-chat-composer-attachments.ts   |  89 +++---
 ...-native-chat-composer-image-input.test.tsx |   6 +-
 ...omposer-paste-session-attachments.test.tsx |  17 +-
 .../use-native-chat-composer-paste.test.tsx   |  36 ++-
 .../use-native-chat-composer-paste.ts         | 114 ++++----
 ...-native-chat-external-attachments.test.tsx |  13 +-
 ...e-native-chat-menu-paste-lifetime.test.tsx | 273 ++++++++++++++++++
 .../use-native-chat-paste-lifetime.test.tsx   | 141 +++++++++
 .../use-native-chat-paste-lifetime.ts         |  87 ++++--
 33 files changed, 1524 insertions(+), 350 deletions(-)
 create mode 100644 src/main/window/clipboard-image-source.test.ts
 create mode 100644 src/main/window/clipboard-image-source.ts
 create mode 100644 src/renderer/src/components/native-chat/native-chat-composer-paste-options.ts
 create mode 100644 src/renderer/src/components/native-chat/native-chat-composer-upload-completion.test.tsx
 create mode 100644 src/renderer/src/components/native-chat/native-chat-prompt-document-text.test.ts
 create mode 100644 src/renderer/src/components/native-chat/native-chat-prompt-document-text.ts
 create mode 100644 src/renderer/src/components/native-chat/use-native-chat-menu-paste-lifetime.test.tsx
 create mode 100644 src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.test.tsx

diff --git a/src/main/window/clipboard-agent-session-attachment-paste.test.ts b/src/main/window/clipboard-agent-session-attachment-paste.test.ts
index 8db77235abf..ba32e82c3b9 100644
--- a/src/main/window/clipboard-agent-session-attachment-paste.test.ts
+++ b/src/main/window/clipboard-agent-session-attachment-paste.test.ts
@@ -10,7 +10,11 @@ const mocks = vi.hoisted(() => ({
 
 vi.mock('electron', () => ({
   app: { getPath: vi.fn(() => '/tmp/client-user-data') },
-  clipboard: { readImage: mocks.readImage },
+  clipboard: {
+    readImage: mocks.readImage,
+    availableFormats: () => ['image/png'],
+    readBuffer: () => Buffer.alloc(0)
+  },
   ipcMain: { removeHandler: vi.fn(), handle: mocks.handle },
   nativeImage: { createFromBuffer: vi.fn() }
 }))
diff --git a/src/main/window/clipboard-image-source.test.ts b/src/main/window/clipboard-image-source.test.ts
new file mode 100644
index 00000000000..cebd03f1959
--- /dev/null
+++ b/src/main/window/clipboard-image-source.test.ts
@@ -0,0 +1,72 @@
+import { describe, expect, it, vi } from 'vitest'
+import { readClipboardImageSource } from './clipboard-image-source'
+
+function clipboardReader(filePath = '', itemCount = 1, formats: string[] = ['FileNameW']) {
+  const shellItems = Buffer.alloc(4 + 4 * (itemCount + 1))
+  shellItems.writeUInt32LE(itemCount)
+  const buffers: Record<string, Buffer> = {
+    FileNameW: Buffer.from(`${filePath}\0`, 'utf16le'),
+    'Shell IDList Array': shellItems
+  }
+  return {
+    availableFormats: vi.fn(() => formats),
+    readBuffer: vi.fn((format: string) => buffers[format] ?? Buffer.alloc(0))
+  }
+}
+
+describe('readClipboardImageSource', () => {
+  it.each(['darwin', 'linux', 'win32'] as const)(
+    'recognizes native image formats on %s without decoding',
+    (platform) => {
+      const clipboard = clipboardReader('', 1, ['text/plain', 'image/png'])
+      expect(readClipboardImageSource(clipboard, platform)).toEqual({
+        kind: 'native',
+        windowsFileFormats: null
+      })
+    }
+  )
+
+  it.each(['darwin', 'linux', 'win32'] as const)('ignores ordinary text on %s', (platform) => {
+    expect(readClipboardImageSource(clipboardReader('', 1, ['text/plain']), platform)).toBeNull()
+  })
+
+  it.each([
+    'C:\\Users\\alice\\图片\\shot.PNG',
+    '\\\\server\\share\\shot.jpeg',
+    '\\\\?\\C:\\Users\\alice\\shot.jpg',
+    '\\\\?\\UNC\\server\\share\\shot.png'
+  ])('recognizes a supported single Windows image file: %s', (filePath) => {
+    const clipboard = clipboardReader(filePath)
+    const source = readClipboardImageSource(clipboard, 'win32')
+    expect(source?.kind).toBe('windows-file')
+    expect(source?.windowsFileFormats).toEqual({
+      fileNameW: clipboard.readBuffer('FileNameW'),
+      shellIdListArray: clipboard.readBuffer('Shell IDList Array')
+    })
+  })
+
+  it.each([
+    ['C:\\shot.pdf', 1],
+    ['C:\\shot.webp', 1],
+    ['C:\\shot.png', 2],
+    ['shot.png', 1],
+    ['C:shot.png', 1],
+    ['\\\\server\\pipe\\shot.png', 1],
+    ['C:\\one.png\0C:\\two.png', 1]
+  ])('rejects an unsupported file source: %s (%s items)', (filePath, itemCount) => {
+    expect(readClipboardImageSource(clipboardReader(filePath, itemCount), 'win32')).toBeNull()
+  })
+
+  it.each(['darwin', 'linux'] as const)('never reads Windows file formats on %s', (platform) => {
+    const clipboard = clipboardReader('C:\\shot.png')
+    expect(readClipboardImageSource(clipboard, platform)).toBeNull()
+    expect(clipboard.readBuffer).not.toHaveBeenCalled()
+  })
+
+  it('keeps the copied-file fallback beside advertised native image data', () => {
+    const clipboard = clipboardReader('C:\\shot.png', 1, ['image/png', 'FileNameW'])
+    const source = readClipboardImageSource(clipboard, 'win32')
+    expect(source?.kind).toBe('native')
+    expect(source?.windowsFileFormats?.fileNameW).toEqual(clipboard.readBuffer('FileNameW'))
+  })
+})
diff --git a/src/main/window/clipboard-image-source.ts b/src/main/window/clipboard-image-source.ts
new file mode 100644
index 00000000000..f5dc72a0247
--- /dev/null
+++ b/src/main/window/clipboard-image-source.ts
@@ -0,0 +1,33 @@
+import { clipboardFormatsIncludeImage } from '../../shared/clipboard-image'
+import {
+  readWindowsCopiedImageFilePath,
+  type WindowsClipboardFileFormats
+} from './clipboard-windows-image-file'
+
+type ClipboardImageReader = {
+  availableFormats: () => string[]
+  readBuffer: (format: string) => Buffer
+}
+
+type ClipboardImageSource =
+  | { kind: 'native'; windowsFileFormats: WindowsClipboardFileFormats | null }
+  | { kind: 'windows-file'; windowsFileFormats: WindowsClipboardFileFormats }
+
+/** Select image sources without decoding pixels or reading a copied file. */
+export function readClipboardImageSource(
+  clipboard: ClipboardImageReader,
+  platform: NodeJS.Platform = process.platform
+): ClipboardImageSource | null {
+  const formats =
+    platform === 'win32'
+      ? {
+          fileNameW: clipboard.readBuffer('FileNameW'),
+          shellIdListArray: clipboard.readBuffer('Shell IDList Array')
+        }
+      : null
+  const windowsFileFormats = formats && readWindowsCopiedImageFilePath(formats) ? formats : null
+  if (clipboardFormatsIncludeImage(clipboard.availableFormats())) {
+    return { kind: 'native', windowsFileFormats }
+  }
+  return windowsFileFormats ? { kind: 'windows-file', windowsFileFormats } : null
+}
diff --git a/src/main/window/clipboard-ipc-handlers.test.ts b/src/main/window/clipboard-ipc-handlers.test.ts
index 2d283a50de2..dc7168f7d65 100644
--- a/src/main/window/clipboard-ipc-handlers.test.ts
+++ b/src/main/window/clipboard-ipc-handlers.test.ts
@@ -226,6 +226,7 @@ describe('registerClipboardHandlers', () => {
     clipboardReadBufferMock.mockReset()
     clipboardReadBufferMock.mockReturnValue(Buffer.alloc(0))
     clipboardWriteTextMock.mockReset()
+    clipboardAvailableFormatsMock.mockReturnValue(['image/png'])
     clipboardReadImageMock.mockReset()
     clipboardWriteImageMock.mockReset()
     clipboardWriteBufferMock.mockReset()
@@ -571,62 +572,72 @@ describe('registerClipboardHandlers', () => {
     }
   })
 
-  it('routes a Windows Explorer FileNameW image through the target-aware attachment flow', async () => {
-    const platformSpy = vi.spyOn(process, 'platform', 'get').mockReturnValue('win32')
-    const sourcePath = 'C:\\Users\\alice\\图片\\copied-image.png'
-    const png = Buffer.from([4, 3, 2, 1])
-    clipboardReadImageMock.mockReturnValue({ isEmpty: () => true })
-    clipboardReadBufferMock.mockImplementation((format: string) =>
-      format === 'FileNameW' ? Buffer.from(`${sourcePath}\0`, 'utf16le') : shellIdListArray(1)
-    )
-    const source = Buffer.alloc(24)
-    Buffer.from([137, 80, 78, 71, 13, 10, 26, 10]).copy(source)
-    source.writeUInt32BE(13, 8)
-    source.write('IHDR', 12, 'ascii')
-    source.writeUInt32BE(1, 16)
-    source.writeUInt32BE(1, 20)
-    const close = vi.fn().mockResolvedValue(undefined)
-    fsOpenMock.mockResolvedValue({
-      close,
-      stat: vi.fn().mockResolvedValue({ isFile: () => true, size: source.byteLength }),
-      read: vi.fn(async (buffer: Buffer, offset: number, length: number, position: number) => {
-        const bytesRead = Math.min(Math.max(source.byteLength - position, 0), length)
-        source.copy(buffer, offset, position, position + bytesRead)
-        return { buffer, bytesRead }
+  it.each([false, true])(
+    'routes a Windows Explorer image with native format advertised: %s',
+    async (advertisesImage) => {
+      setTrustedClipboardRendererWebContentsId(17)
+      const platformSpy = vi.spyOn(process, 'platform', 'get').mockReturnValue('win32')
+      clipboardAvailableFormatsMock.mockReturnValue(
+        advertisesImage ? ['image/png', 'FileNameW'] : ['FileNameW']
+      )
+      const sourcePath = 'C:\\Users\\alice\\图片\\copied-image.png'
+      const png = Buffer.from([4, 3, 2, 1])
+      clipboardReadImageMock.mockReturnValue({ isEmpty: () => true })
+      clipboardReadBufferMock.mockImplementation((format: string) =>
+        format === 'FileNameW' ? Buffer.from(`${sourcePath}\0`, 'utf16le') : shellIdListArray(1)
+      )
+      const source = Buffer.alloc(24)
+      Buffer.from([137, 80, 78, 71, 13, 10, 26, 10]).copy(source)
+      source.writeUInt32BE(13, 8)
+      source.write('IHDR', 12, 'ascii')
+      source.writeUInt32BE(1, 16)
+      source.writeUInt32BE(1, 20)
+      const close = vi.fn().mockResolvedValue(undefined)
+      fsOpenMock.mockResolvedValue({
+        close,
+        stat: vi.fn().mockResolvedValue({ isFile: () => true, size: source.byteLength }),
+        read: vi.fn(async (buffer: Buffer, offset: number, length: number, position: number) => {
+          const bytesRead = Math.min(Math.max(source.byteLength - position, 0), length)
+          source.copy(buffer, offset, position, position + bytesRead)
+          return { buffer, bytesRead }
+        })
+      })
+      nativeImageCreateFromBufferMock.mockReturnValue({
+        getSize: () => ({ height: 1, width: 1 }),
+        isEmpty: () => false,
+        toPNG: () => png
+      })
+      const writeFileBase64 = vi.fn().mockResolvedValue(undefined)
+      getSshFilesystemProviderMock.mockReturnValue({
+        getTempDir: vi.fn().mockResolvedValue('/var/tmp'),
+        writeFileBase64
       })
-    })
-    nativeImageCreateFromBufferMock.mockReturnValue({
-      getSize: () => ({ height: 1, width: 1 }),
-      isEmpty: () => false,
-      toPNG: () => png
-    })
-    const writeFileBase64 = vi.fn().mockResolvedValue(undefined)
-    getSshFilesystemProviderMock.mockReturnValue({
-      getTempDir: vi.fn().mockResolvedValue('/var/tmp'),
-      writeFileBase64
-    })
 
-    try {
-      registerClipboardHandlers({} as never)
+      try {
+        registerClipboardHandlers({} as never)
 
-      const handler = getRegisteredHandlers().get('clipboard:saveImageAsTempFile')
-      await expect(handler?.(makeClipboardEvent(), { connectionId: 'ssh-1' })).resolves.toBe(
-        '/var/tmp/orca-paste-1760000000000-00000000-0000-4000-8000-000000000000.png'
-      )
-      expect(clipboardReadBufferMock).toHaveBeenCalledWith('FileNameW')
-      expect(clipboardReadBufferMock).toHaveBeenCalledWith('Shell IDList Array')
-      expect(fsOpenMock).toHaveBeenCalledWith(sourcePath, 'r')
-      expect(nativeImageCreateFromBufferMock).toHaveBeenCalledWith(source)
-      expect(close).toHaveBeenCalled()
-      expect(writeFileBase64).toHaveBeenCalledWith(
-        '/var/tmp/orca-paste-1760000000000-00000000-0000-4000-8000-000000000000.png',
-        png.toString('base64')
-      )
-      expect(fsWriteFileMock).not.toHaveBeenCalled()
-    } finally {
-      platformSpy.mockRestore()
+        const probe = getRegisteredHandlers().get('clipboard:hasImage')
+        expect(probe?.(makeClipboardEvent())).toBe(true)
+        expect(() => probe?.(makeClipboardEvent({ id: 42 }))).toThrow()
+        const handler = getRegisteredHandlers().get('clipboard:saveImageAsTempFile')
+        await expect(handler?.(makeClipboardEvent(), { connectionId: 'ssh-1' })).resolves.toBe(
+          '/var/tmp/orca-paste-1760000000000-00000000-0000-4000-8000-000000000000.png'
+        )
+        expect(clipboardReadBufferMock).toHaveBeenCalledWith('FileNameW')
+        expect(clipboardReadBufferMock).toHaveBeenCalledWith('Shell IDList Array')
+        expect(fsOpenMock).toHaveBeenCalledWith(sourcePath, 'r')
+        expect(nativeImageCreateFromBufferMock).toHaveBeenCalledWith(source)
+        expect(close).toHaveBeenCalled()
+        expect(writeFileBase64).toHaveBeenCalledWith(
+          '/var/tmp/orca-paste-1760000000000-00000000-0000-4000-8000-000000000000.png',
+          png.toString('base64')
+        )
+        expect(fsWriteFileMock).not.toHaveBeenCalled()
+      } finally {
+        platformSpy.mockRestore()
+      }
     }
-  })
+  )
 
   it('saves clipboard images through the selected remote runtime host', async () => {
     const png = Buffer.alloc(512 * 1024)
@@ -874,18 +885,4 @@ describe('registerClipboardHandlers', () => {
     expect(nativeImageCreateFromBufferMock).toHaveBeenCalled()
     expect(clipboardWriteImageMock).not.toHaveBeenCalled()
   })
-
-  it.each([
-    [['text/plain'], false],
-    [['text/plain', 'image/png'], true]
-  ])('reports image presence for %j from the format list without decoding', (formats, expected) => {
-    setTrustedClipboardRendererWebContentsId(17)
-    clipboardAvailableFormatsMock.mockReturnValue(formats)
-    // oxlint-disable-next-line typescript/consistent-type-assertions -- SAFETY: registering handlers never reads the store for clipboard image presence.
-    registerClipboardHandlers({} as never)
-    const probe = getRegisteredHandlers().get('clipboard:hasImage')
-    expect(probe?.(makeClipboardEvent())).toBe(expected)
-    expect(clipboardReadImageMock).not.toHaveBeenCalled()
-    expect(() => probe?.(makeClipboardEvent({ id: 42 }))).toThrow()
-  })
 })
diff --git a/src/main/window/clipboard-ipc-handlers.ts b/src/main/window/clipboard-ipc-handlers.ts
index 05a09a54bb8..80dad3bd02b 100644
--- a/src/main/window/clipboard-ipc-handlers.ts
+++ b/src/main/window/clipboard-ipc-handlers.ts
@@ -25,7 +25,6 @@ import {
   assertClipboardImageBase64LengthWithinLimit,
   assertClipboardImageByteLengthWithinLimit,
   assertClipboardImageDimensionsWithinLimit,
-  clipboardFormatsIncludeImage,
   type ClipboardImageThumbnail
 } from '../../shared/clipboard-image'
 import {
@@ -41,6 +40,7 @@ import {
 import { saveClipboardImageBufferInRuntime } from './clipboard-runtime-image-upload'
 import { uploadPastedImageToAgentSessionAttachments } from '../ipc/agent-session-attachment-upload'
 import { readWindowsClipboardImageFileAsPng } from './clipboard-windows-image-file'
+import { readClipboardImageSource } from './clipboard-image-source'
 import { readClipboardCopiedFilePaths } from './clipboard-copied-file-paths'
 import { buildClipboardImageThumbnail } from './clipboard-image-thumbnail'
 import { writeClipboardTextAndVerify } from './clipboard-text-write-verify'
@@ -141,7 +141,7 @@ export function registerClipboardHandlers(store: Store): void {
   })
   ipcMain.handle('clipboard:hasImage', (event): boolean => {
     assertTrustedClipboardSender(event)
-    return clipboardFormatsIncludeImage(clipboard.availableFormats())
+    return readClipboardImageSource(clipboard) !== null
   })
   // Why: a file-manager copy also carries the files' names as text, which a paste must not type.
   ipcMain.handle('clipboard:readFilePaths', (event): string[] => {
@@ -155,21 +155,19 @@ export function registerClipboardHandlers(store: Store): void {
     'clipboard:saveImageAsTempFile',
     async (event, args?: SaveClipboardImageAsTempFileArgs) => {
       assertTrustedClipboardSender(event)
+      const source = readClipboardImageSource(clipboard)
+      if (!source) {
+        return null
+      }
       const image = clipboard.readImage()
       if (image.isEmpty()) {
-        if (process.platform !== 'win32') {
+        if (!source.windowsFileFormats) {
           return null
         }
-        const copiedFilePng = await readWindowsClipboardImageFileAsPng(
-          {
-            fileNameW: clipboard.readBuffer('FileNameW'),
-            shellIdListArray: clipboard.readBuffer('Shell IDList Array')
-          },
-          {
-            createImageFromBuffer: (buffer) => nativeImage.createFromBuffer(buffer),
-            openFile: (filePath) => open(filePath, 'r')
-          }
-        )
+        const copiedFilePng = await readWindowsClipboardImageFileAsPng(source.windowsFileFormats, {
+          createImageFromBuffer: (buffer) => nativeImage.createFromBuffer(buffer),
+          openFile: (filePath) => open(filePath, 'r')
+        })
         return copiedFilePng ? saveClipboardImageBufferForTarget(copiedFilePng, args) : null
       }
       assertClipboardImageDimensionsWithinLimit(image.getSize())
diff --git a/src/main/window/clipboard-runtime-owned-ssh-paste.test.ts b/src/main/window/clipboard-runtime-owned-ssh-paste.test.ts
index 1bc2915508f..e2844455c38 100644
--- a/src/main/window/clipboard-runtime-owned-ssh-paste.test.ts
+++ b/src/main/window/clipboard-runtime-owned-ssh-paste.test.ts
@@ -15,13 +15,14 @@ const PNG = Buffer.from([0, 1, 2, 3])
 vi.mock('electron', () => ({
   app: { getPath: vi.fn(() => '/tmp') },
   clipboard: {
+    availableFormats: () => ['image/png'],
     readImage: () => ({
       getSize: () => ({ height: 1, width: 1 }),
       isEmpty: () => false,
       toPNG: () => PNG
     }),
     readText: vi.fn(),
-    readBuffer: vi.fn(),
+    readBuffer: vi.fn(() => Buffer.alloc(0)),
     writeText: vi.fn(),
     writeImage: vi.fn(),
     writeBuffer: vi.fn()
diff --git a/src/main/window/clipboard-windows-image-file.ts b/src/main/window/clipboard-windows-image-file.ts
index 39099332958..17baa100846 100644
--- a/src/main/window/clipboard-windows-image-file.ts
+++ b/src/main/window/clipboard-windows-image-file.ts
@@ -84,6 +84,15 @@ export function readWindowsCopiedFilePath({
   return hasAtMostOneShellItem(shellIdListArray) ? decodeFileNameW(fileNameW) : null
 }
 
+export function readWindowsCopiedImageFilePath(
+  formats: WindowsClipboardFileFormats
+): string | null {
+  const filePath = readWindowsCopiedFilePath(formats)
+  return filePath && IMAGE_FILE_EXTENSION_SET.has(win32.extname(filePath).toLowerCase())
+    ? filePath
+    : null
+}
+
 function readPngDimensions(source: Buffer): { height: number; width: number } | null {
   if (
     source.byteLength < 24 ||
@@ -164,8 +173,8 @@ export async function readWindowsClipboardImageFileAsPng(
   formats: WindowsClipboardFileFormats,
   { createImageFromBuffer, openFile }: WindowsClipboardImageFileDeps
 ): Promise<Buffer | null> {
-  const filePath = readWindowsCopiedFilePath(formats)
-  if (!filePath || !IMAGE_FILE_EXTENSION_SET.has(win32.extname(filePath).toLowerCase())) {
+  const filePath = readWindowsCopiedImageFilePath(formats)
+  if (!filePath) {
     return null
   }
 
diff --git a/src/renderer/src/components/native-chat/NativeChatComposer.paste-remount.test.tsx b/src/renderer/src/components/native-chat/NativeChatComposer.paste-remount.test.tsx
index f5509b5b10d..327397db8b0 100644
--- a/src/renderer/src/components/native-chat/NativeChatComposer.paste-remount.test.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatComposer.paste-remount.test.tsx
@@ -4,23 +4,41 @@
 // replaces the composer. The real composer, attachment and paste hooks keep the upload, and Send
 // waits for it, whenever the composer comes back; a rich-text paste's image is owed from the start.
 
-import { act, cleanup, render } from '@testing-library/react'
+import { act, cleanup, fireEvent, render, screen, waitFor } from '@testing-library/react'
 import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
-import type { ClipboardEventLike } from './native-chat-clipboard-payload'
+import { createRef, type RefObject } from 'react'
+import type { NativeChatComposerHandle } from './native-chat-composer-types'
+import type { NativeChatAttachmentOwner } from './native-chat-attachment-upload'
+import type {
+  NativeChatComposerField as NativeChatComposerFieldComponent,
+  NativeChatComposerFieldProps,
+  NativeChatComposerImageAttachment
+} from './NativeChatComposerField'
 
 type FieldProps = {
-  onPaste?: (event: ClipboardEventLike) => void
-  imageAttachments?: { path: string; pending?: boolean }[]
+  imageAttachments?: readonly NativeChatComposerImageAttachment[]
   sendButtonDisabled?: boolean
+  onRemoveImageAttachment: (id: string) => void
 }
 
 const mocks = vi.hoisted(() => {
-  const state: { fieldProps: FieldProps | null } = { fieldProps: null }
+  const state: { fieldProps: FieldProps | null; owner: NativeChatAttachmentOwner } = {
+    fieldProps: null,
+    owner: {
+      kind: 'runtime-session',
+      environmentId: 'env-1',
+      pairingRevision: 1,
+      sessionId: 'session-1'
+    }
+  }
   return { state, prepare: vi.fn(), save: vi.fn() }
 })
 
 vi.mock('../../store', () => {
   const state = {
+    tabsByWorktree: {},
+    worktrees: [],
+    repos: [],
     dictationState: 'idle',
     settings: { voice: { enabled: false }, nativeChatSessionOptions: {} },
     agentStatusByPaneKey: {},
@@ -43,24 +61,25 @@ vi.mock('@/lib/native-chat-telemetry', () => ({
   emitNativeChatPickerOpened: vi.fn(),
   emitNativeChatSendClassified: vi.fn()
 }))
-vi.mock('./NativeChatComposerField', () => ({
-  NativeChatComposerField: (props: FieldProps) => {
-    mocks.state.fieldProps = props
-    return <div data-testid="native-chat-composer-field" />
+vi.mock('./NativeChatComposerField', async (importOriginal) => {
+  const original = await importOriginal<{
+    NativeChatComposerField: typeof NativeChatComposerFieldComponent
+  }>()
+  return {
+    NativeChatComposerField: (props: NativeChatComposerFieldProps) => {
+      mocks.state.fieldProps = props
+      return <original.NativeChatComposerField {...props} />
+    }
   }
-}))
+})
+vi.mock('./NativeChatComposerActions', () => ({ NativeChatComposerActions: () => null }))
 vi.mock('./use-native-chat-skills', () => ({
   useNativeChatSkills: () => ({ status: 'ready', skills: [], error: null, retry: () => {} })
 }))
 vi.mock('./use-native-chat-external-attachments', () => ({
   useNativeChatExternalAttachments: () => ({
     attachExternalPaths: vi.fn(),
-    resolveAttachmentOwner: () => ({
-      kind: 'runtime-session',
-      environmentId: 'env-1',
-      pairingRevision: 1,
-      sessionId: 'session-1'
-    })
+    resolveAttachmentOwner: () => mocks.state.owner
   })
 }))
 vi.mock('./native-chat-attachment-upload', async (importOriginal) => ({
@@ -71,6 +90,7 @@ vi.mock('./native-chat-attachment-upload', async (importOriginal) => ({
 import { NativeChatComposer } from './NativeChatComposer'
 import {
   clearNativeChatDraftCacheForTests,
+  readNativeChatDraftCache,
   writeNativeChatDraftCache
 } from './native-chat-draft-cache'
 import {
@@ -81,9 +101,13 @@ import {
 const PANE = 'tab-1::session-1'
 const STORED = '/srv/agent-session-attachments/0b6f8a52-4a3e-4c4e-9a59-1d5d1f2b8c01/orca-paste.png'
 
-function composer(): React.JSX.Element {
+function composer(
+  acceptsImages = true,
+  composerRef?: RefObject<NativeChatComposerHandle | null>
+): React.JSX.Element {
   return (
     <NativeChatComposer
+      ref={composerRef}
       terminalTabId="tab-1"
       paneKey={PANE}
       targetPtyId={null}
@@ -100,6 +124,7 @@ function composer(): React.JSX.Element {
         optionSnapshot: [],
         onError: vi.fn(),
         runtime: 'remote',
+        acceptsImages,
         sessionId: 'session-1',
         runtimeEnvironmentId: 'env-1'
       }}
@@ -123,7 +148,7 @@ function installPreloadApi(ui: Record<string, unknown>): void {
   })
 }
 
-function imagePaste(text?: string): ClipboardEventLike {
+function imagePaste(text?: string): ClipboardEvent {
   const data = new DataTransfer()
   data.items.add(new File(['image'], 'image.png', { type: 'image/png' }))
   if (text) {
@@ -147,6 +172,12 @@ beforeEach(() => {
   clearNativeChatAttachmentCacheForTests()
   clearNativeChatDraftCacheForTests()
   mocks.state.fieldProps = null
+  mocks.state.owner = {
+    kind: 'runtime-session',
+    environmentId: 'env-1',
+    pairingRevision: 1,
+    sessionId: 'session-1'
+  }
   mocks.prepare.mockResolvedValue({
     ok: true,
     target: {
@@ -163,7 +194,9 @@ beforeEach(() => {
 })
 
 afterEach(() => {
+  vi.useRealTimers()
   cleanup()
+  vi.restoreAllMocks()
   vi.unstubAllGlobals()
 })
 
@@ -177,7 +210,7 @@ describe('a paste into a chat on a paired server', () => {
     )
     installPreloadApi({ saveClipboardImageAsTempFile: mocks.save })
     const view = render(composer())
-    await act(async () => mocks.state.fieldProps?.onPaste?.(imagePaste()))
+    await act(async () => fireEvent(screen.getByRole('textbox'), imagePaste()))
     expect(mocks.state.fieldProps?.imageAttachments).toMatchObject([{ pending: true }])
 
     // The agent asks a question: its card takes the composer's place while the image uploads.
@@ -196,7 +229,7 @@ describe('a paste into a chat on a paired server', () => {
     // Something typed, so only the pending image can hold Send.
     writeNativeChatDraftCache(PANE, 'look at this')
     const first = render(composer())
-    await act(async () => mocks.state.fieldProps?.onPaste?.(imagePaste()))
+    await act(async () => fireEvent(screen.getByRole('textbox'), imagePaste()))
     first.unmount()
 
     // Back from the prompt card while the image is still on its way to the server.
@@ -217,7 +250,7 @@ describe('a paste into a chat on a paired server', () => {
     writeNativeChatDraftCache(PANE, 'look at this caption')
     render(composer())
     expect(mocks.state.fieldProps?.sendButtonDisabled).toBe(false)
-    await act(async () => mocks.state.fieldProps?.onPaste?.(imagePaste('caption')))
+    await act(async () => fireEvent(screen.getByRole('textbox'), imagePaste('caption')))
 
     // The text is in; the image is not yet anywhere, but it is owed to this message.
     expect(mocks.state.fieldProps?.sendButtonDisabled).toBe(true)
@@ -229,7 +262,7 @@ describe('a paste into a chat on a paired server', () => {
     const finishUpload = holdUpload()
     writeNativeChatDraftCache(PANE, 'look at this caption')
     const first = render(composer())
-    await act(async () => mocks.state.fieldProps?.onPaste?.(imagePaste('caption')))
+    await act(async () => fireEvent(screen.getByRole('textbox'), imagePaste('caption')))
     // A prompt card replaces the composer while the server is still being asked.
     first.unmount()
     render(composer())
@@ -254,3 +287,155 @@ describe('a paste into a chat on a paired server', () => {
     expect(mocks.state.fieldProps?.imageAttachments).toMatchObject([{ path: STORED }])
   })
 })
+
+it('keeps a local image paste after the real composer closes and reopens', async () => {
+  mocks.state.owner = { kind: 'local' }
+  mocks.save.mockClear()
+  const finishUpload = holdUpload()
+  const first = render(composer())
+  await act(async () => fireEvent(screen.getByRole('textbox'), imagePaste()))
+  await waitFor(() => expect(mocks.save).toHaveBeenCalled())
+  expect(mocks.state.fieldProps?.imageAttachments).toMatchObject([{ pending: true }])
+  first.unmount()
+  await act(async () => finishUpload('/local/native-chat-pastes/orca-paste-1-image.png'))
+  render(composer())
+  expect(mocks.state.fieldProps?.imageAttachments).toMatchObject([
+    { path: '/local/native-chat-pastes/orca-paste-1-image.png' }
+  ])
+  await waitFor(() => expect(mocks.state.fieldProps?.imageAttachments?.[0]?.pending).toBeFalsy())
+})
+
+it.each([
+  { kind: 'local', acceptsImages: false },
+  { kind: 'ssh', acceptsImages: false },
+  { kind: 'local', acceptsImages: true },
+  { kind: 'ssh', acceptsImages: true }
+] as const)(
+  'can remove a stalled $kind paste after reopen with acceptsImages=$acceptsImages',
+  async ({ kind, acceptsImages }) => {
+    mocks.state.owner =
+      kind === 'local'
+        ? { kind: 'local' }
+        : {
+            kind: 'ssh',
+            connectionId: 'ssh-1',
+            worktreePath: '/remote/folder',
+            expectedExecutionHostId: 'ssh:ssh-1',
+            expectedSshTargetId: 'ssh-1',
+            expectedSshConnectionGeneration: 1
+          }
+    vi.useFakeTimers({ toFake: ['setTimeout', 'clearTimeout', 'Date'] })
+    const finishUpload = holdUpload()
+    writeNativeChatDraftCache(PANE, 'look at this')
+    const first = render(composer(acceptsImages))
+    expect(mocks.state.fieldProps?.sendButtonDisabled).toBe(false)
+    await act(async () => fireEvent(screen.getByRole('textbox'), imagePaste()))
+    first.unmount()
+    render(composer(acceptsImages))
+    await act(async () => vi.advanceTimersByTimeAsync(24 * 60 * 60 * 1000))
+    expect(mocks.state.fieldProps?.sendButtonDisabled).toBe(true)
+    expect(screen.getByRole('button', { name: 'Saving pasted image…' })).toBeTruthy()
+    await act(async () =>
+      fireEvent.click(screen.getByRole('button', { name: 'Remove attachment' }))
+    )
+    expect(mocks.state.fieldProps?.sendButtonDisabled).toBe(false)
+    await act(async () =>
+      finishUpload(
+        kind === 'local'
+          ? '/local/native-chat-pastes/orca-paste-1-image.png'
+          : '/tmp/orca-paste-1-image.png'
+      )
+    )
+    expect(readNativeChatAttachmentCache(PANE)).toEqual([])
+    expect(readNativeChatDraftCache(PANE)).toBe('look at this')
+    expect(mocks.state.fieldProps?.imageAttachments).toEqual([])
+  }
+)
+
+it.each([true, false])(
+  'pastes ordinary menu text without image feedback or holding Send, acceptsImages=%s',
+  async (acceptsImages) => {
+    mocks.state.owner = { kind: 'local' }
+    mocks.save.mockClear()
+    mocks.save.mockReturnValue(new Promise(() => {}))
+    installPreloadApi({
+      saveClipboardImageAsTempFile: mocks.save,
+      readClipboardText: async () => 'ordinary text',
+      readClipboardFilePaths: async () => [],
+      readClipboardImageThumbnail: async () => null,
+      clipboardHasImage: async () => false
+    })
+    const handle = createRef<NativeChatComposerHandle>()
+    writeNativeChatDraftCache(PANE, 'look at this')
+    render(composer(acceptsImages, handle))
+    await act(async () => handle.current?.pasteFromClipboard())
+    expect(screen.getByRole('textbox').textContent).toContain('ordinary text')
+    expect(screen.queryByRole('button', { name: 'Saving pasted image…' })).toBeNull()
+    expect(mocks.state.fieldProps?.sendButtonDisabled).toBe(false)
+    expect(mocks.save).not.toHaveBeenCalled()
+  }
+)
+
+it.each([true, false])(
+  'releases all previews when a paired paste is removed before acceptance, acceptsImages=%s',
+  async (acceptsImages) => {
+    const prepare = Promise.withResolvers<{
+      ok: true
+      target: {
+        environmentId: string
+        sessionId: string
+        expectedEnvironmentPairingRevision: number
+      }
+    }>()
+    mocks.prepare.mockReturnValue(prepare.promise)
+    const finishUpload = holdUpload()
+    const allocated = new Set<string>()
+    const released = new Set<string>()
+    vi.spyOn(URL, 'createObjectURL').mockImplementation(() => {
+      const url = 'blob:late-acceptance'
+      allocated.add(url)
+      return url
+    })
+    vi.spyOn(URL, 'revokeObjectURL').mockImplementation((url) => {
+      released.add(url)
+    })
+    const view = render(composer(acceptsImages))
+    await act(async () => fireEvent(screen.getByRole('textbox'), imagePaste('caption')))
+    await act(async () =>
+      fireEvent.click(screen.getByRole('button', { name: 'Remove attachment' }))
+    )
+    await act(async () =>
+      prepare.resolve({
+        ok: true,
+        target: {
+          environmentId: 'env-1',
+          sessionId: 'session-1',
+          expectedEnvironmentPairingRevision: 1
+        }
+      })
+    )
+    await act(async () => finishUpload(STORED))
+    expect(readNativeChatAttachmentCache(PANE)).toEqual([])
+    view.unmount()
+    expect([...allocated].filter((url) => !released.has(url))).toEqual([])
+  }
+)
+
+it('starts no upload when the composer closes before image presence is known', async () => {
+  mocks.state.owner = { kind: 'local' }
+  mocks.save.mockClear()
+  const presence = Promise.withResolvers<boolean>()
+  installPreloadApi({
+    saveClipboardImageAsTempFile: mocks.save,
+    readClipboardText: async () => '',
+    readClipboardFilePaths: async () => [],
+    clipboardHasImage: () => presence.promise
+  })
+  const handle = createRef<NativeChatComposerHandle>()
+  const view = render(composer(true, handle))
+  await act(async () => handle.current?.pasteFromClipboard())
+  view.unmount()
+  await act(async () => presence.resolve(true))
+  expect(mocks.save).not.toHaveBeenCalled()
+  expect(readNativeChatAttachmentCache(PANE)).toEqual([])
+})
diff --git a/src/renderer/src/components/native-chat/NativeChatComposer.tsx b/src/renderer/src/components/native-chat/NativeChatComposer.tsx
index f9519ed859f..62315c377ec 100644
--- a/src/renderer/src/components/native-chat/NativeChatComposer.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatComposer.tsx
@@ -197,6 +197,7 @@ const NativeChatComposerPane = forwardRef<NativeChatComposerHandle, NativeChatCo
     })
 
     const handlePasteEvent = useNativeChatComposerHandle(ref, {
+      attachmentScopeKey: draftScopeKey,
       textareaRef,
       caret,
       draft,
diff --git a/src/renderer/src/components/native-chat/NativeChatComposerField.tsx b/src/renderer/src/components/native-chat/NativeChatComposerField.tsx
index 0abc1c22bc6..b39d6548170 100644
--- a/src/renderer/src/components/native-chat/NativeChatComposerField.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatComposerField.tsx
@@ -100,8 +100,6 @@ export type NativeChatComposerImageAttachment = {
   pending?: boolean
   /** The file's name while it uploads: a dropped or picked file, not a pasted image. */
   pendingName?: string
-  /** Owed to the message but not shown yet: a rich-text paste's image while its server is asked. */
-  hidden?: true
   /** Set on an image the draft names but can't send: the file to attach again. */
   unavailableName?: string
 }
@@ -174,7 +172,6 @@ export function NativeChatComposerField({
   sessionOptionsPickerRequest,
   goalMode
 }: NativeChatComposerFieldProps): React.JSX.Element {
-  const shownAttachments = imageAttachments.filter((attachment) => !attachment.hidden)
   const draftNotSaved = useNativeChatComposerDraftUnsaved(draftScopeKey)
   const optionCount =
     autocomplete.mode === 'slash'
@@ -282,9 +279,9 @@ export function NativeChatComposerField({
               '[contain:paint]'
             )}
           >
-            {shownAttachments.length > 0 ? (
+            {imageAttachments.length > 0 ? (
               <div className="mb-2 flex flex-wrap gap-2 px-1 pt-1.5">
-                {shownAttachments.map((attachment) => (
+                {imageAttachments.map((attachment) => (
                   <NativeChatImageAttachmentPreview
                     key={attachment.id}
                     attachment={attachment}
diff --git a/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.test.ts b/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.test.ts
index 25782727d40..7c11c95b2b5 100644
--- a/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.test.ts
+++ b/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.test.ts
@@ -115,4 +115,45 @@ describe('native-chat composer draft addition', () => {
     expect(next.drafts.readNativeChatDraftCache('agent-session:s2')).toBe('please go\n\ngo')
     expect(storage.drafts.get('agent-session:s2')?.text).toBe('please go\n\ngo')
   })
+
+  it.each(['delayed load', 'crash replay'])(
+    'keeps picked nodes when appending through %s',
+    async (mode) => {
+      const document = {
+        type: 'doc',
+        content: [
+          {
+            type: 'paragraph',
+            content: [
+              { type: 'nativeChatSkill', attrs: { token: '$review' } },
+              { type: 'text', text: '-long' }
+            ]
+          }
+        ]
+      }
+      storage.drafts.set(SCOPE, { text: '$review-long', document, images: [], savedAt: 1 })
+      let next: DraftModules
+      if (mode === 'crash replay') {
+        const crashed = await reload({
+          using: { ...storage, write: () => new Promise<void>(() => {}) }
+        })
+        crashed.drafts.appendNativeChatDraftCache(SCOPE, '@/stored/file.pdf')
+        crashed.store.clearNativeChatComposerDraftsForTests()
+        next = await reload()
+      } else {
+        const { using, land } = slowLoading()
+        next = await reload({ using, hydrate: false })
+        await next.store.waitForNativeChatComposerDrafts(1)
+        next.drafts.appendNativeChatDraftCache(SCOPE, '@/stored/file.pdf')
+        land()
+        await next.store.waitForNativeChatComposerDrafts(1_000)
+      }
+      await next.store.nativeChatComposerDraftWritesSettled()
+      expect(next.drafts.readNativeChatDraftCache(SCOPE)).toBe('$review-long\n\n@/stored/file.pdf')
+      expect(next.store.readNativeChatComposerDraft(SCOPE).document?.content?.[0]).toEqual(
+        document.content[0]
+      )
+      expect(storage.drafts.get(SCOPE)?.document?.content?.[0]).toEqual(document.content[0])
+    }
+  )
 })
diff --git a/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.ts b/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.ts
index 76b82af5393..441ce2264cc 100644
--- a/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.ts
+++ b/src/renderer/src/components/native-chat/native-chat-composer-draft-addition.ts
@@ -3,6 +3,7 @@
 // loaded later, or replayed from the journal after a crash.
 
 import { appendReturnedDraftText } from '../../../../shared/returned-draft-text'
+import { appendPromptDocumentText } from './native-chat-prompt-document-text'
 import { basename } from '@/lib/path'
 import type {
   NativeChatComposerDraft,
@@ -25,7 +26,7 @@ export function withNativeChatComposerDraftAddition(
   draft: NativeChatComposerDraft,
   addition: NativeChatComposerDraftAddition,
   options: { once?: boolean } = {}
-): Pick<NativeChatComposerDraft, 'text' | 'images'> {
+): Pick<NativeChatComposerDraft, 'text' | 'images' | 'document'> {
   const text = appendReturnedDraftText(draft.text, addition.text ?? '')
   const images = [...draft.images]
   for (const { id, path, connectionId } of addition.images ?? []) {
@@ -42,5 +43,5 @@ export function withNativeChatComposerDraftAddition(
       images[placeholder] = image
     }
   }
-  return { text, images }
+  return { text, images, document: appendPromptDocumentText(draft.document, draft.text, text) }
 }
diff --git a/src/renderer/src/components/native-chat/native-chat-composer-draft-journal.ts b/src/renderer/src/components/native-chat/native-chat-composer-draft-journal.ts
index c1b979e3645..dc4a210d6cc 100644
--- a/src/renderer/src/components/native-chat/native-chat-composer-draft-journal.ts
+++ b/src/renderer/src/components/native-chat/native-chat-composer-draft-journal.ts
@@ -145,7 +145,6 @@ export function replayNativeChatComposerDraftJournal(
     drafts.set(scopeKey, {
       ...from,
       ...next,
-      ...(next.text === from.text ? {} : { document: undefined }),
       savedAt: at
     })
     changed.add(scopeKey)
diff --git a/src/renderer/src/components/native-chat/native-chat-composer-draft-store.ts b/src/renderer/src/components/native-chat/native-chat-composer-draft-store.ts
index 60dddf06d2f..2842251fd6a 100644
--- a/src/renderer/src/components/native-chat/native-chat-composer-draft-store.ts
+++ b/src/renderer/src/components/native-chat/native-chat-composer-draft-store.ts
@@ -189,7 +189,7 @@ function withAddition<T extends NativeChatComposerDraft>(
   options: { once?: boolean } = {}
 ): T {
   const next = withNativeChatComposerDraftAddition(draft, addition, options)
-  return { ...draft, ...next, ...(next.text === draft.text ? {} : { document: undefined }) }
+  return { ...draft, ...next }
 }
 
 /**
@@ -206,13 +206,13 @@ export function appendToNativeChatComposerDraft(
 ): boolean {
   const before = records.get(scopeKey)
   const current = readNativeChatComposerDraft(scopeKey)
-  const { text, images } = withAddition(current, addition)
+  const { text, images, document } = withAddition(current, addition)
   updateNativeChatComposerDraft(
     scopeKey,
     {
       text,
       images,
-      ...(text === current.text ? {} : { document: undefined }),
+      document,
       ...(owner ? { owner } : {})
     },
     'immediate',
diff --git a/src/renderer/src/components/native-chat/native-chat-composer-paste-options.ts b/src/renderer/src/components/native-chat/native-chat-composer-paste-options.ts
new file mode 100644
index 00000000000..1d4a17d41f9
--- /dev/null
+++ b/src/renderer/src/components/native-chat/native-chat-composer-paste-options.ts
@@ -0,0 +1,23 @@
+import type { AgentType } from '../../../../shared/agent-status-types'
+import type { NativeChatAttachmentOwner } from './native-chat-attachment-upload'
+
+export type UseNativeChatComposerPasteArgs = {
+  targetKey?: string
+  attachmentScopeKey?: string
+  agent: AgentType
+  /** Re-read after awaits so a mid-paste disable guards the composer. */
+  disabled: boolean
+  caret: number
+  /** Resolved at paste time: SSH panes must save the clipboard image on the
+   *  remote host, or the attached path names a file the agent cannot read. */
+  resolveAttachmentOwner: () => NativeChatAttachmentOwner
+  attachResolvedPaths: (paths: string[], connectionId?: string | null) => void
+  beginPendingImageAttachment: (previewUrl?: string, pendingName?: string) => string | null
+  resolvePendingImageAttachment: (id: string, path: string, connectionId?: string | null) => void
+  /** Supplies a pending chip's thumbnail. */
+  revealPendingImageAttachment?: (id: string, previewUrl?: string) => void
+  dropPendingImageAttachment: (id: string) => void
+  insertTypedText: (text: string) => boolean
+  setCaret: (caret: number) => void
+  setNotice: (notice: string | null, errorText?: string) => void
+}
diff --git a/src/renderer/src/components/native-chat/native-chat-composer-upload-completion.test.tsx b/src/renderer/src/components/native-chat/native-chat-composer-upload-completion.test.tsx
new file mode 100644
index 00000000000..97d06b69b52
--- /dev/null
+++ b/src/renderer/src/components/native-chat/native-chat-composer-upload-completion.test.tsx
@@ -0,0 +1,230 @@
+// @vitest-environment happy-dom
+import { createRef } from 'react'
+import { act, cleanup, render, renderHook } from '@testing-library/react'
+import { afterEach, beforeEach, expect, it, vi } from 'vitest'
+import { useNativeChatComposerAttachments } from './use-native-chat-composer-attachments'
+import { attachNativeChatSessionAttachmentPaths } from './native-chat-session-attachment-drop'
+import { NativeChatPromptEditor } from './NativeChatPromptEditor'
+import type { NativeChatComposerInput } from './native-chat-composer-input'
+import {
+  clearNativeChatComposerDraftsForTests,
+  hydrateNativeChatComposerDrafts,
+  nativeChatComposerDraftWritesSettled,
+  readNativeChatComposerDraft,
+  structuredAgentSessionDraftScopeKey as scope,
+  updateNativeChatComposerDraft
+} from './native-chat-composer-draft-store'
+import {
+  createMemoryNativeChatComposerDraftStorage,
+  setNativeChatComposerDraftStorageForTests
+} from './native-chat-composer-draft-storage'
+import {
+  clearNativeChatPendingAttachmentsForTests,
+  nativeChatPendingAttachmentSnapshot,
+  takeNativeChatPendingAttachment
+} from './native-chat-pending-attachment-cache'
+
+// Only host replies are controlled; pending-chip ownership and upload completion are production code.
+vi.mock('@/runtime/runtime-rpc-client', () => ({
+  callRuntimeRpc: vi.fn(async () => ({
+    runtimeId: 'paired-host',
+    capabilities: ['agent-session.attachments.v1']
+  }))
+}))
+let previousApi: typeof window.api
+beforeEach(async () => {
+  previousApi = window.api
+  setNativeChatComposerDraftStorageForTests(createMemoryNativeChatComposerDraftStorage())
+  await hydrateNativeChatComposerDrafts()
+})
+afterEach(async () => {
+  cleanup()
+  await nativeChatComposerDraftWritesSettled()
+  clearNativeChatPendingAttachmentsForTests()
+  clearNativeChatComposerDraftsForTests()
+  window.api = previousApi
+})
+async function uploadFixture(
+  extension: string,
+  { removed = false, withSkill = false, switchScope = false } = {}
+) {
+  const path = `/srv/agent-session-attachments/u1/report.${extension}`
+  const sourcePath = `/local/report.${extension}`
+  let finish = () => {}
+  Object.defineProperty(window, 'api', {
+    configurable: true,
+    writable: true,
+    value: {
+      fs: {
+        uploadPathsToAgentSessionAttachments: () =>
+          new Promise((resolve) => {
+            finish = () => resolve({ uploaded: [{ sourcePath, path }], skipped: [], failed: [] })
+          })
+      }
+    }
+  })
+  updateNativeChatComposerDraft(scope('a'), { text: 'next question' }, 'immediate')
+  if (withSkill) {
+    const inputRef = createRef<NativeChatComposerInput>()
+    const picker = render(
+      <NativeChatPromptEditor
+        scopeKey={scope('a')}
+        inputRef={inputRef}
+        initialValue="$rev"
+        disabled={false}
+        placeholder="Message"
+        onChange={(input) =>
+          updateNativeChatComposerDraft(scope('a'), { text: input.value }, 'immediate')
+        }
+        onSelect={() => {}}
+      />
+    )
+    act(() => {
+      inputRef.current?.insertSkill?.(0, 4, '$review')
+      if (inputRef.current) {
+        inputRef.current.value = '$review-long'
+      }
+    })
+    await vi.waitFor(() =>
+      expect(picker.container.querySelector('[data-native-chat-skill]')).not.toBeNull()
+    )
+    picker.unmount()
+  }
+  const textareaRef = createRef<NativeChatComposerInput>()
+  const view = renderHook(
+    ({ draftScope }) => {
+      return useNativeChatComposerAttachments({
+        attachmentScopeKey: draftScope,
+        allowWithoutTarget: true,
+        caret: 0,
+        disabled: false,
+        isComposing: () => false,
+        resolveTarget: () => null,
+        textareaRef,
+        setCaret: () => {},
+        setDraft: (updater) =>
+          updateNativeChatComposerDraft(
+            draftScope,
+            { text: updater(readNativeChatComposerDraft(draftScope).text) },
+            'immediate'
+          ),
+        setNotice: () => {}
+      })
+    },
+    { initialProps: { draftScope: scope('a') } }
+  )
+  let uploaded = Promise.resolve()
+  act(() => {
+    uploaded = attachNativeChatSessionAttachmentPaths({
+      paths: [sourcePath],
+      owner: {
+        kind: 'runtime-session',
+        environmentId: 'paired',
+        sessionId: 'a',
+        pairingRevision: 1
+      },
+      chips: view.result.current.pendingChips,
+      isAbandoned: () => false,
+      ownerStillCurrent: () => true,
+      setNotice: () => {}
+    })
+  })
+  await Promise.resolve()
+  await Promise.resolve()
+  const chip = nativeChatPendingAttachmentSnapshot(scope('a'))[0]
+  if (!chip) {
+    throw new Error('Expected pending upload chip')
+  }
+  expect(chip.pendingName).toBe(`report.${extension}`)
+  const targetScope = scope('a')
+  if (switchScope) {
+    act(() => view.rerender({ draftScope: scope('b') }))
+    render(
+      <NativeChatPromptEditor
+        scopeKey={scope('b')}
+        inputRef={textareaRef}
+        initialValue="other question"
+        disabled={false}
+        placeholder="Message"
+        onChange={(input) =>
+          updateNativeChatComposerDraft(scope('b'), { text: input.value }, 'immediate')
+        }
+        onSelect={() => {}}
+      />
+    )
+  }
+  if (removed) {
+    act(() => takeNativeChatPendingAttachment(targetScope, chip.id))
+  }
+  if (!switchScope) {
+    view.unmount()
+  }
+  finish()
+  await uploaded
+  return {
+    path,
+    targetScope,
+    other: readNativeChatComposerDraft(scope('b')),
+    otherInput: textareaRef.current?.value,
+    target: readNativeChatComposerDraft(targetScope),
+    pending: nativeChatPendingAttachmentSnapshot(targetScope)
+  }
+}
+it.each(['pdf', 'png'])(
+  'settles an unmounted paired %s upload in its owning draft',
+  async (extension) => {
+    const result = await uploadFixture(extension)
+    expect(result.pending).toEqual([])
+    if (extension === 'pdf') {
+      expect(result.target.text).toContain(`@${result.path}`)
+    } else {
+      expect(result.target.images[0]?.path).toBe(result.path)
+    }
+    expect(result.other.text).toBe('')
+    expect(result.other.images).toEqual([])
+  }
+)
+
+it('does not attach a file reference removed while uploading', async () => {
+  const result = await uploadFixture('pdf', { removed: true })
+  expect(result.pending).toEqual([])
+  expect(result.target.text).toBe('next question')
+})
+
+it('keeps the original file owner when the mounted composer switches draft scopes', async () => {
+  const result = await uploadFixture('pdf', { switchScope: true })
+  expect(result.pending).toEqual([])
+  expect(result.target.text).toBe(`next question\n\n@${result.path}`)
+  expect(result.otherInput).toBe('other question')
+  expect(result.other.images).toEqual([])
+})
+
+it.each(['pdf', 'png'])(
+  'preserves a picked skill and its literal suffix after an unmounted %s upload',
+  async (extension) => {
+    const result = await uploadFixture(extension, { withSkill: true })
+    expect(result.pending).toEqual([])
+    const inputRef = createRef<NativeChatComposerInput>()
+    const view = render(
+      <NativeChatPromptEditor
+        scopeKey={result.targetScope}
+        inputRef={inputRef}
+        initialValue={result.target.text}
+        disabled={false}
+        placeholder="Message"
+        onChange={() => {}}
+        onSelect={() => {}}
+      />
+    )
+    expect(inputRef.current?.value).toContain('$review-long')
+    if (extension === 'pdf') {
+      expect(inputRef.current?.value).toContain(`@${result.path}`)
+    } else {
+      expect(result.target.images[0]?.path).toBe(result.path)
+    }
+    await vi.waitFor(() => {
+      expect(view.container.querySelectorAll('[data-native-chat-skill]')).toHaveLength(1)
+      expect(view.container.querySelector('[data-native-chat-skill]')?.textContent).toBe('Review')
+    })
+  }
+)
diff --git a/src/renderer/src/components/native-chat/native-chat-draft-cache.ts b/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
index 8d086d5ac35..f4f7eee53bd 100644
--- a/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
+++ b/src/renderer/src/components/native-chat/native-chat-draft-cache.ts
@@ -1,5 +1,6 @@
 import type { NativeChatComposerImageAttachment } from './NativeChatComposerField'
 import type { JSONContent } from '@tiptap/react'
+import type { NativeChatComposerDraftOwner } from './native-chat-composer-draft-storage'
 // The composer's in-progress draft text and its editor document, keyed by the same stable pane
 // scope as image attachments. The composer unmounts when the pane toggles back to the hosted
 // terminal, so without this the typed-but-unsent draft would be lost on every TUI/GUI round-trip.
@@ -40,13 +41,17 @@ const appendListeners = new Map<string, Set<(text: string, previous: string) =>
 
 /** Puts text back after whatever is typed, and tells a mounted composer to show it. True once it
  *  is durable, so the copy it came from may go. */
-export function appendNativeChatDraftCache(scopeKey: string, text: string): boolean {
+export function appendNativeChatDraftCache(
+  scopeKey: string,
+  text: string,
+  owner?: NativeChatComposerDraftOwner
+): boolean {
   if (text === '') {
     return true
   }
   const previous = readNativeChatDraftCache(scopeKey)
   // Durable now: the copy it came from (a send handed back, a queued card) goes right after this.
-  const durable = appendToNativeChatComposerDraft(scopeKey, { text })
+  const durable = appendToNativeChatComposerDraft(scopeKey, { text }, owner)
   appendListeners.get(scopeKey)?.forEach((listener) => listener(text, previous))
   return durable
 }
diff --git a/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.test.ts b/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.test.ts
index 3dccd946f89..96a187899a1 100644
--- a/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.test.ts
+++ b/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.test.ts
@@ -1,13 +1,12 @@
-import { afterEach, describe, expect, it, vi } from 'vitest'
+import { afterEach, describe, expect, it } from 'vitest'
 import {
   addNativeChatPendingAttachment,
   clearNativeChatPendingAttachmentsForTests,
   dropNativeChatPendingAttachmentsForTab,
   dropNativeChatPendingAttachmentsOwnedBy,
   nativeChatPendingAttachmentSnapshot,
-  revealNativeChatPendingAttachment,
   settleNativeChatPendingAttachment,
-  subscribeToNativeChatPendingAttachments,
+  settleNativeChatPendingAttachmentReferences,
   takeNativeChatPendingAttachment
 } from './native-chat-pending-attachment-cache'
 import {
@@ -58,22 +57,6 @@ describe('the pane pending attachment cache', () => {
     expect(takeNativeChatPendingAttachment('pane-b', 'b1')).toBeUndefined()
   })
 
-  it('shows a hidden chip and tells every subscriber, with a new snapshot only on change', () => {
-    const listener = vi.fn()
-    const unsubscribe = subscribeToNativeChatPendingAttachments('pane-c', listener)
-    addNativeChatPendingAttachment('pane-c', { id: 'c1', path: '', pending: true, hidden: true })
-    const hidden = nativeChatPendingAttachmentSnapshot('pane-c')
-
-    expect(nativeChatPendingAttachmentSnapshot('pane-c')).toBe(hidden)
-    revealNativeChatPendingAttachment('pane-c', 'c1')
-
-    expect(nativeChatPendingAttachmentSnapshot('pane-c')).toEqual([
-      { id: 'c1', path: '', pending: true }
-    ])
-    expect(listener).toHaveBeenCalledTimes(2)
-    unsubscribe()
-  })
-
   it('settles into a draft owned by the workspace it began in, after its chat stopped naming one', () => {
     const conversation = structuredAgentSessionDraftScopeKey('session-1')
     let open = true
@@ -89,6 +72,25 @@ describe('the pane pending attachment cache', () => {
     expect(readNativeChatComposerDraft(conversation).images).toEqual([])
   })
 
+  it('keeps reference settlement owned by the workspace after its chat closes', () => {
+    const conversation = structuredAgentSessionDraftScopeKey('session-1')
+    let open = true
+    setNativeChatComposerDraftOwnerResolver((scopeKey) =>
+      open && scopeKey === conversation ? OWNER : undefined
+    )
+    addPending(conversation, 'file')
+    open = false
+
+    settleNativeChatPendingAttachmentReferences(conversation, [
+      { id: 'file', path: '/store/a.pdf' }
+    ])
+
+    expect(readNativeChatComposerDraft(conversation).text).toBe('@/store/a.pdf')
+    expect(nativeChatPendingAttachmentSnapshot(conversation)).toEqual([])
+    deleteNativeChatComposerDraftsOwnedBy(OWNER)
+    expect(readNativeChatComposerDraft(conversation).text).toBe('')
+  })
+
   it('drops the chips begun in a removed workspace on that host only', () => {
     const resolved = new Map<string, NativeChatComposerDraftOwner>([
       ['tab-1:leaf', OWNER],
diff --git a/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.ts b/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.ts
index 3d4e477d0ce..a2c771a6568 100644
--- a/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.ts
+++ b/src/renderer/src/components/native-chat/native-chat-pending-attachment-cache.ts
@@ -1,15 +1,11 @@
-// A composer's chips still on their way (a save, an upload, a server's answer), per pane scope,
-// owned here rather than by the composer. A prompt card unmounts the composer, so anything owed to
-// the message must outlive it: the composer that comes back shows the same chips, Send waits for
-// them, and each settles into the scope's draft whichever composer, if any, is showing. They are
-// never saved with the draft, so a restored draft cannot bring back an upload as if it were
-// attached. Every chip dies with its operation: settled or dropped when the save or upload settles
-// (each bounded by its call timeout), removed by the user, or dropped with the drafts of a tab or
-// workspace the user closed or removed, so none settles into a draft nothing could find or delete.
+// Pending operations belong to draft scopes and outlive their composers. They are not persisted.
+// Completion, failure, explicit removal, draft/workspace deletion or renderer exit ends ownership.
 
 import { useCallback, useSyncExternalStore } from 'react'
 import type { NativeChatComposerImageAttachment } from './NativeChatComposerField'
 import type { NativeChatComposerDraftOwner } from './native-chat-composer-draft-storage'
+import { appendNativeChatDraftCache } from './native-chat-draft-cache'
+import { formatNativeChatFileReference } from '../../../../shared/agent-image-paste'
 import {
   appendToNativeChatComposerDraft,
   nativeChatDraftScopeTabId,
@@ -115,17 +111,23 @@ export function settleNativeChatPendingAttachment(
   return true
 }
 
-/** Shows a pending chip that was held out of sight, such as while a server was asked first. */
-export function revealNativeChatPendingAttachment(scopeKey: string, id: string): void {
-  const current = nativeChatPendingAttachmentSnapshot(scopeKey)
-  if (current.some((attachment) => attachment.id === id && attachment.hidden)) {
-    writePending(
-      scopeKey,
-      current.map((attachment) => {
-        const { hidden: _hidden, ...shown } = attachment
-        return attachment.id === id ? shown : attachment
-      })
-    )
+/** File results settle only while their operation still belongs to this draft. */
+export function settleNativeChatPendingAttachmentReferences(
+  scopeKey: string,
+  references: { id: string; path: string }[],
+  insertAtCaret?: (paths: string[]) => void
+): void {
+  const owner = pendingOwners.get(scopeKey)
+  const paths = references.flatMap(({ id, path }) =>
+    takeNativeChatPendingAttachment(scopeKey, id) ? [path] : []
+  )
+  if (paths.length === 0) {
+    return
+  }
+  if (insertAtCaret) {
+    insertAtCaret(paths)
+  } else {
+    appendNativeChatDraftCache(scopeKey, paths.map(formatNativeChatFileReference).join(' '), owner)
   }
 }
 
diff --git a/src/renderer/src/components/native-chat/native-chat-prompt-document-text.test.ts b/src/renderer/src/components/native-chat/native-chat-prompt-document-text.test.ts
new file mode 100644
index 00000000000..24f3056c1ee
--- /dev/null
+++ b/src/renderer/src/components/native-chat/native-chat-prompt-document-text.test.ts
@@ -0,0 +1,66 @@
+import { expect, it } from 'vitest'
+import { withNativeChatComposerDraftAddition } from './native-chat-composer-draft-addition'
+import type { NativeChatComposerDraft } from './native-chat-composer-draft-storage'
+
+it.each(['spaces', 'hard breaks', 'empty paragraphs'])(
+  'trims trailing %s while keeping picked skills and earlier paragraphs',
+  (trailing) => {
+    const first = { type: 'paragraph', content: [{ type: 'text', text: 'first' }] }
+    const picked = { type: 'nativeChatSkill', attrs: { token: '$review' } }
+    const draft: NativeChatComposerDraft = {
+      text: `first\n$review${trailing === 'spaces' ? '  ' : '\n\n'}`,
+      images: [],
+      document: {
+        type: 'doc',
+        content: [
+          first,
+          {
+            type: 'paragraph',
+            content: [
+              picked,
+              ...(trailing === 'spaces'
+                ? [{ type: 'text', text: '  ' }]
+                : trailing === 'hard breaks'
+                  ? [{ type: 'hardBreak' }, { type: 'hardBreak' }]
+                  : [])
+            ]
+          },
+          ...(trailing === 'empty paragraphs'
+            ? [
+                { type: 'paragraph', content: [] },
+                { type: 'paragraph', content: [] }
+              ]
+            : [])
+        ]
+      }
+    }
+    const result = withNativeChatComposerDraftAddition(draft, { text: 'go' })
+    expect(result.text).toBe('first\n$review\n\ngo')
+    expect(result.document?.content).toEqual([
+      first,
+      { type: 'paragraph', content: [picked] },
+      { type: 'paragraph', content: [] },
+      { type: 'paragraph', content: [{ type: 'text', text: 'go' }] }
+    ])
+  }
+)
+
+it('replaces an all-whitespace document with literal returned text', () => {
+  const result = withNativeChatComposerDraftAddition(
+    {
+      text: ' \n',
+      images: [],
+      document: {
+        type: 'doc',
+        content: [
+          { type: 'paragraph', content: [{ type: 'text', text: ' ' }] },
+          { type: 'paragraph', content: [] }
+        ]
+      }
+    },
+    { text: '$review' }
+  )
+  expect(result.document?.content).toEqual([
+    { type: 'paragraph', content: [{ type: 'text', text: '$review' }] }
+  ])
+})
diff --git a/src/renderer/src/components/native-chat/native-chat-prompt-document-text.ts b/src/renderer/src/components/native-chat/native-chat-prompt-document-text.ts
new file mode 100644
index 00000000000..6151a994c95
--- /dev/null
+++ b/src/renderer/src/components/native-chat/native-chat-prompt-document-text.ts
@@ -0,0 +1,59 @@
+import type { JSONContent } from '@tiptap/react'
+
+export function promptTextContent(text: string): JSONContent {
+  return {
+    type: 'doc',
+    content: text.split('\n').map((line) => ({
+      type: 'paragraph',
+      content: line ? [{ type: 'text', text: line }] : []
+    }))
+  }
+}
+
+/** Applies an appended text change without replacing existing picked nodes. */
+export function appendPromptDocumentText(
+  document: JSONContent | undefined,
+  before: string,
+  after: string
+): JSONContent | undefined {
+  if (!document || before === after) {
+    return document
+  }
+  const kept = before.trimEnd()
+  if (kept === '') {
+    return promptTextContent(after)
+  }
+  const blocks = [...(document.content ?? [])]
+  while (blocks.length > 0) {
+    const block = blocks.pop()
+    const content = [...(block?.content ?? [])]
+    while (content.length > 0) {
+      const node = content.at(-1)
+      if (node?.type === 'hardBreak') {
+        content.pop()
+      } else if (node?.type === 'text') {
+        const text = node.text?.trimEnd() ?? ''
+        if (text === '') {
+          content.pop()
+        } else {
+          content[content.length - 1] = { ...node, text }
+          break
+        }
+      } else {
+        break
+      }
+    }
+    if (content.length > 0 && block) {
+      const [first, ...rest] = promptTextContent(after.slice(kept.length)).content ?? []
+      return {
+        ...document,
+        content: [
+          ...blocks,
+          { ...block, content: [...content, ...(first?.content ?? [])] },
+          ...rest
+        ]
+      }
+    }
+  }
+  return promptTextContent(after)
+}
diff --git a/src/renderer/src/components/native-chat/native-chat-prompt-document.ts b/src/renderer/src/components/native-chat/native-chat-prompt-document.ts
index 7ed5fd8c130..96bba1a75fd 100644
--- a/src/renderer/src/components/native-chat/native-chat-prompt-document.ts
+++ b/src/renderer/src/components/native-chat/native-chat-prompt-document.ts
@@ -1,6 +1,7 @@
 import { NativeChatSkillPill } from './NativeChatSkillPill'
-import { ReactNodeViewRenderer, Node, type JSONContent } from '@tiptap/react'
+import { ReactNodeViewRenderer, Node } from '@tiptap/react'
 import type { Node as ProseMirrorNode } from '@tiptap/pm/model'
+export { promptTextContent } from './native-chat-prompt-document-text'
 
 export const NativeChatSkill = Node.create({
   name: 'nativeChatSkill',
@@ -24,16 +25,6 @@ export const NativeChatSkill = Node.create({
   ]
 })
 
-export function promptTextContent(text: string): JSONContent {
-  return {
-    type: 'doc',
-    content: text.split('\n').map((line) => ({
-      type: 'paragraph',
-      content: line ? [{ type: 'text', text: line }] : []
-    }))
-  }
-}
-
 /** Each boundary maps a plain-text caret to a document position, including atomic skills. */
 export function promptTextMap(doc: ProseMirrorNode): { text: string; positions: number[] } {
   let text = ''
diff --git a/src/renderer/src/components/native-chat/native-chat-session-attachment-drop.ts b/src/renderer/src/components/native-chat/native-chat-session-attachment-drop.ts
index 0d655d8de8a..e51be382d94 100644
--- a/src/renderer/src/components/native-chat/native-chat-session-attachment-drop.ts
+++ b/src/renderer/src/components/native-chat/native-chat-session-attachment-drop.ts
@@ -18,7 +18,7 @@ export type NativeChatPendingAttachmentChips = {
   drop: (id: string) => boolean
   /** Adds stored files as `@path` references to the scope's draft, which keeps them through an
    *  input-method composition or a remount. */
-  attachReferences: (paths: string[]) => void
+  attachReferences: (references: { id: string; path: string }[]) => void
 }
 
 /**
@@ -86,7 +86,7 @@ export async function attachNativeChatSessionAttachmentPaths(args: {
     return
   }
   const notAttached: { name: string; reason: string }[] = []
-  const references: string[] = []
+  const references: { id: string; path: string }[] = []
   for (const { path, chipId } of pending) {
     const storedPath = stored.get(path)
     if (!storedPath) {
@@ -100,9 +100,7 @@ export async function attachNativeChatSessionAttachmentPaths(args: {
       continue
     }
     // Other files become `@path` references, as every attach does, unless their chip was removed.
-    if (args.chips.drop(chipId)) {
-      references.push(storedPath)
-    }
+    references.push({ id: chipId, path: storedPath })
   }
   // Inserting at the caret clears the notice, so what failed is said after.
   if (references.length > 0) {
diff --git a/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.test.tsx b/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.test.tsx
index 5208dfe6e8a..ddf55907789 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.test.tsx
+++ b/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.test.tsx
@@ -477,13 +477,14 @@ describe('useNativeChatComposerAttachments', () => {
   it('keeps an upload that finishes while the composer is unmounted, for when it returns', async () => {
     const probe = await renderProbe('pty-gone')
     const chips = probe.latest().pendingChips
-    const begun: { image?: string | null; removed?: string | null } = {}
+    const begun: { image?: string | null; removed?: string | null; reference?: string | null } = {}
     act(() => {
       begun.image = chips.begin(undefined, 'shot.png')
       begun.removed = chips.begin(undefined, 'old.png')
+      begun.reference = chips.begin(undefined, 'notes.pdf')
     })
-    const { image, removed } = begun
-    if (!image || !removed) {
+    const { image, removed, reference } = begun
+    if (!image || !removed || !reference) {
       throw new Error('expected pending chips')
     }
     act(() => probe.latest().removeImageAttachment(removed))
@@ -492,7 +493,7 @@ describe('useNativeChatComposerAttachments', () => {
 
     chips.resolve(image, '/srv/agent-session-attachments/u1/shot.png')
     chips.resolve(removed, '/srv/agent-session-attachments/u2/old.png')
-    chips.attachReferences(['/srv/agent-session-attachments/u3/notes.pdf'])
+    chips.attachReferences([{ id: reference, path: '/srv/agent-session-attachments/u3/notes.pdf' }])
 
     expect(readNativeChatAttachmentCache('pty-gone')).toEqual([
       { id: image, path: '/srv/agent-session-attachments/u1/shot.png' }
@@ -531,11 +532,33 @@ describe('useNativeChatComposerAttachments', () => {
     act(() => back.root.unmount())
   })
 
+  it('gives uploads unique IDs across composers remounted in the same clock tick', async () => {
+    const now = vi.spyOn(Date, 'now').mockReturnValue(1_000)
+    try {
+      const first = await renderProbe('pty-ids', true)
+      const ids: (string | null)[] = []
+      act(() => ids.push(first.latest().pendingChips.begin(undefined, 'first.pdf')))
+      act(() => first.root.unmount())
+      const next = await renderProbe('pty-ids', true)
+      act(() => ids.push(next.latest().pendingChips.begin(undefined, 'second.pdf')))
+      expect(new Set(ids).size).toBe(2)
+      expect(nativeChatPendingAttachmentSnapshot('pty-ids')).toHaveLength(2)
+      act(() => next.root.unmount())
+    } finally {
+      now.mockRestore()
+    }
+  })
+
   it('inserts a stored file at the caret while the composer is showing and not composing', async () => {
     const probe = await renderProbe('pty-caret', true)
-    act(() =>
-      probe.latest().pendingChips.attachReferences(['/srv/agent-session-attachments/u6/a.pdf'])
-    )
+    act(() => {
+      const chips = probe.latest().pendingChips
+      const id = chips.begin(undefined, 'a.pdf')
+      if (!id) {
+        throw new Error('expected pending chip')
+      }
+      chips.attachReferences([{ id, path: '/srv/agent-session-attachments/u6/a.pdf' }])
+    })
     expect(probe.draft()).toBe('@/srv/agent-session-attachments/u6/a.pdf ')
     expect(readNativeChatDraftCache('pty-caret')).toBe('')
     act(() => probe.root.unmount())
@@ -555,8 +578,7 @@ describe('useNativeChatComposerAttachments', () => {
     const id: string = chipId
     // The upload finishes mid-composition: the reference waits for the composition to settle.
     act(() => {
-      expect(chips.drop(id)).toBe(true)
-      chips.attachReferences(['/srv/agent-session-attachments/u4/notes.pdf'])
+      chips.attachReferences([{ id, path: '/srv/agent-session-attachments/u4/notes.pdf' }])
     })
     // A prompt card takes the composer's place before the composition settles.
     act(() => probe.root.unmount())
diff --git a/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.ts b/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.ts
index b360492493f..2eb20ac7954 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.ts
+++ b/src/renderer/src/components/native-chat/use-native-chat-composer-attachments.ts
@@ -1,12 +1,5 @@
 import type { NativeChatComposerInput } from './native-chat-composer-input'
-import {
-  useCallback,
-  useEffect,
-  useMemo,
-  useRef,
-  useSyncExternalStore,
-  type RefObject
-} from 'react'
+import { useCallback, useEffect, useMemo, useSyncExternalStore, type RefObject } from 'react'
 import {
   nativeChatComposerTargetIsRemote,
   nativeChatLocalAttachmentUnsupportedNotice,
@@ -26,17 +19,15 @@ import type { NativeChatPendingAttachmentChips } from './native-chat-session-att
 import {
   addNativeChatPendingAttachment,
   clearNativeChatPendingAttachments,
-  revealNativeChatPendingAttachment,
   settleNativeChatPendingAttachment,
+  settleNativeChatPendingAttachmentReferences,
+  nativeChatPendingAttachmentSnapshot,
   takeNativeChatPendingAttachment,
   useNativeChatPendingAttachments
 } from './native-chat-pending-attachment-cache'
-import {
-  appendNativeChatAttachmentCache,
-  appendNativeChatDraftCache
-} from './native-chat-draft-cache'
+import { appendNativeChatAttachmentCache } from './native-chat-draft-cache'
 import { useNativeChatComposerAttachmentPreviews } from './use-native-chat-composer-attachment-previews'
-import { formatNativeChatFileReference } from '../../../../shared/agent-image-paste'
+import { createUuidV4 } from '../../../../shared/uuid-v4'
 
 export type UseNativeChatComposerAttachmentsArgs = {
   attachmentScopeKey: string
@@ -75,11 +66,7 @@ export function useNativeChatComposerAttachments({
   clearImageAttachments: () => void
   flushPendingAttachments: () => void
   removeImageAttachment: (id: string) => void
-  beginPendingImageAttachment: (
-    previewUrl?: string,
-    pendingName?: string,
-    options?: { hidden?: true }
-  ) => string | null
+  beginPendingImageAttachment: (previewUrl?: string, pendingName?: string) => string | null
   resolvePendingImageAttachment: (id: string, path: string, connectionId?: string | null) => void
   revealPendingImageAttachment: (id: string, previewUrl?: string) => void
   dropPendingImageAttachment: (id: string) => boolean
@@ -117,19 +104,18 @@ export function useNativeChatComposerAttachments({
     ],
     [pending, previews, restoring, settled]
   )
-  const imageAttachmentCounter = useRef(0)
-  const mountedRef = useRef(true)
+  const mountedRef = useMemo(
+    () => ({ scopeKey: attachmentScopeKey, current: true }),
+    [attachmentScopeKey]
+  )
   useEffect(() => {
     mountedRef.current = true
     return () => {
       mountedRef.current = false
     }
-  }, [])
+  }, [mountedRef])
 
-  const nextAttachmentId = useCallback((): string => {
-    imageAttachmentCounter.current += 1
-    return `${Date.now()}-${imageAttachmentCounter.current}`
-  }, [])
+  const nextAttachmentId = useCallback(() => createUuidV4(), [])
 
   // Client-local paths cannot cross into a runtime target; workspace-owned
   // paths may only bypass this after the internal drop ownership gate.
@@ -181,10 +167,8 @@ export function useNativeChatComposerAttachments({
   // Placeholder chip shown the instant a paste starts, so a clipboard image that
   // takes a beat to save (or upload over SSH) never reads as a dropped paste.
   const beginPendingImageAttachment = useCallback(
-    (previewUrl?: string, pendingName?: string, options?: { hidden?: true }): string | null => {
-      // Without image input the saved paste is attached by path once it lands, so no image chip;
-      // a named upload chip is a file, not an image, and still shows.
-      if (disabledRef.current || (!acceptsImages && pendingName === undefined)) {
+    (previewUrl?: string, pendingName?: string): string | null => {
+      if (disabledRef.current) {
         return null
       }
       if (attachmentTargetBlocked()) {
@@ -196,14 +180,12 @@ export function useNativeChatComposerAttachments({
         id,
         path: '',
         pending: true,
-        ...(pendingName ? { pendingName } : {}),
-        ...(options?.hidden ? { hidden: true } : {})
+        ...(pendingName ? { pendingName } : {})
       })
       setPreview(id, previewUrl)
       return id
     },
     [
-      acceptsImages,
       attachmentScopeKey,
       attachmentTargetBlocked,
       disabledRef,
@@ -213,17 +195,35 @@ export function useNativeChatComposerAttachments({
     ]
   )
 
+  const attachPendingReferences = useCallback(
+    (references: { id: string; path: string }[]) => {
+      settleNativeChatPendingAttachmentReferences(
+        attachmentScopeKey,
+        references,
+        mountedRef.current && !disabledRef.current && !isComposing()
+          ? (paths) => attachResolvedPaths(paths, null)
+          : undefined
+      )
+    },
+    [attachResolvedPaths, attachmentScopeKey, disabledRef, isComposing, mountedRef]
+  )
+
   const resolvePendingImageAttachment = useCallback(
     (id: string, path: string, connectionId?: string | null) => {
-      settleNativeChatPendingAttachment(attachmentScopeKey, id, path, connectionId)
+      if (acceptsImages) {
+        settleNativeChatPendingAttachment(attachmentScopeKey, id, path, connectionId)
+      } else {
+        attachPendingReferences([{ id, path }])
+      }
     },
-    [attachmentScopeKey]
+    [acceptsImages, attachPendingReferences, attachmentScopeKey]
   )
 
   const revealPendingImageAttachment = useCallback(
     (id: string, previewUrl?: string) => {
-      setPreview(id, previewUrl)
-      revealNativeChatPendingAttachment(attachmentScopeKey, id)
+      if (nativeChatPendingAttachmentSnapshot(attachmentScopeKey).some((chip) => chip.id === id)) {
+        setPreview(id, previewUrl)
+      }
     },
     [attachmentScopeKey, setPreview]
   )
@@ -245,23 +245,12 @@ export function useNativeChatComposerAttachments({
       drop: dropPendingImageAttachment,
       // At the caret, as every attach does; mid-composition or once the composer is gone, into the
       // scope's draft, which keeps it until the composition settles or the composer comes back.
-      attachReferences: (paths) => {
-        if (mountedRef.current && !isComposing()) {
-          attachResolvedPaths(paths, null)
-          return
-        }
-        appendNativeChatDraftCache(
-          attachmentScopeKey,
-          paths.map(formatNativeChatFileReference).join(' ')
-        )
-      }
+      attachReferences: attachPendingReferences
     }),
     [
-      attachResolvedPaths,
-      attachmentScopeKey,
+      attachPendingReferences,
       beginPendingImageAttachment,
       dropPendingImageAttachment,
-      isComposing,
       resolvePendingImageAttachment
     ]
   )
diff --git a/src/renderer/src/components/native-chat/use-native-chat-composer-image-input.test.tsx b/src/renderer/src/components/native-chat/use-native-chat-composer-image-input.test.tsx
index 93e289e4462..71536868356 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-composer-image-input.test.tsx
+++ b/src/renderer/src/components/native-chat/use-native-chat-composer-image-input.test.tsx
@@ -87,10 +87,10 @@ describe('structured composer image input', () => {
     expect(result.pendingChip).not.toBeNull()
   })
 
-  it('references an image by path, with no chip, when the agent takes none', async () => {
+  it('references an image by path, with a removable pending operation, when the agent takes none', async () => {
     const result = await attach(false, '/tmp/shot.png')
-    expect(result.chips).toEqual([])
-    expect(result.pendingChip).toBeNull()
+    expect(result.chips).toEqual([''])
+    expect(result.pendingChip).not.toBeNull()
     expect(result.draft).toContain('/tmp/shot.png')
   })
 
diff --git a/src/renderer/src/components/native-chat/use-native-chat-composer-paste-session-attachments.test.tsx b/src/renderer/src/components/native-chat/use-native-chat-composer-paste-session-attachments.test.tsx
index 421462ae144..e08c92eea4f 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-composer-paste-session-attachments.test.tsx
+++ b/src/renderer/src/components/native-chat/use-native-chat-composer-paste-session-attachments.test.tsx
@@ -49,7 +49,7 @@ vi.stubGlobal('URL', {
 import { useNativeChatComposerPaste } from './use-native-chat-composer-paste'
 
 type HookApi = ReturnType<typeof useNativeChatComposerPaste>
-type Chip = { id: string; path: string; pending: boolean; hidden?: true }
+type Chip = { id: string; path: string; pending: boolean }
 
 const sessionOwner: NativeChatAttachmentOwner = {
   kind: 'runtime-session',
@@ -87,20 +87,18 @@ async function renderPaste(args: {
       setCaret: () => {},
       resolveAttachmentOwner: () => sessionOwner,
       attachResolvedPaths: args.attachResolvedPaths ?? (() => {}),
-      beginPendingImageAttachment: (_preview, _name, options) => {
+      beginPendingImageAttachment: () => {
         counter += 1
         chips.push({
           id: `chip-${counter}`,
           path: '',
-          pending: true,
-          ...(options?.hidden ? { hidden: true } : {})
+          pending: true
         })
         return `chip-${counter}`
       },
       revealPendingImageAttachment: (id) => {
         const chip = chips.find((candidate) => candidate.id === id)
         if (chip) {
-          delete chip.hidden
           revealed += 1
         }
       },
@@ -151,7 +149,7 @@ beforeEach(() => {
   vi.resetAllMocks()
   mocks.readClipboardText.mockResolvedValue('')
   mocks.readClipboardImageThumbnail.mockResolvedValue(null)
-  mocks.clipboardHasImage.mockResolvedValue(false)
+  mocks.clipboardHasImage.mockResolvedValue(true)
   mocks.readClipboardFilePaths.mockResolvedValue([])
   mocks.prepareNativeChatSessionAttachmentUpload.mockResolvedValue({
     ok: true,
@@ -195,11 +193,12 @@ describe('pasting into a structured chat on a paired server', () => {
     expect(probe.chips).toEqual([{ id: 'chip-1', path: storedPath, pending: false }])
   })
 
-  it('attaches the server path when no placeholder chip was shown', async () => {
+  it('settles the server path when no thumbnail was shown', async () => {
     const attachResolvedPaths = vi.fn()
     const probe = await renderPaste({ attachResolvedPaths })
     await act(async () => probe.api().pasteFromClipboard())
-    expect(attachResolvedPaths).toHaveBeenCalledExactlyOnceWith([storedPath], null)
+    expect(probe.chips).toEqual([{ id: 'chip-1', path: storedPath, pending: false }])
+    expect(attachResolvedPaths).not.toHaveBeenCalled()
   })
 
   it('refuses on a server without the attachment store and saves nothing', async () => {
@@ -236,7 +235,7 @@ describe('pasting into a structured chat on a paired server', () => {
     await act(async () => probe.api().handlePaste(imagePasteEvent('caption')))
     expect(insertTypedText).toHaveBeenCalledWith('caption')
     expect(setNotice).not.toHaveBeenCalledWith('needs newer server')
-    // The image was owed to the message only out of sight: no chip showed, so none flashed.
+    // The operation ends quietly when this server cannot store its image.
     expect(probe.begun()).toBe(1)
     expect(probe.revealed()).toBe(0)
     expect(probe.chips).toEqual([])
diff --git a/src/renderer/src/components/native-chat/use-native-chat-composer-paste.test.tsx b/src/renderer/src/components/native-chat/use-native-chat-composer-paste.test.tsx
index cca232c9140..8f42d083208 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-composer-paste.test.tsx
+++ b/src/renderer/src/components/native-chat/use-native-chat-composer-paste.test.tsx
@@ -53,6 +53,7 @@ function createChipStore(): {
   chips: FakeChip[]
   begin: (previewUrl?: string) => string | null
   resolve: (id: string, path: string, connectionId?: string | null) => void
+  reveal: (id: string, previewUrl?: string) => void
   drop: (id: string) => void
   connectionIds: (string | null | undefined)[]
 } {
@@ -62,6 +63,12 @@ function createChipStore(): {
   return {
     chips,
     connectionIds,
+    reveal: (id, previewUrl) => {
+      const chip = chips.find((candidate) => candidate.id === id)
+      if (chip) {
+        chip.previewUrl = previewUrl
+      }
+    },
     begin: (previewUrl) => {
       counter += 1
       const id = `chip-${counter}`
@@ -93,6 +100,7 @@ type ProbeArgs = {
   attachResolvedPaths: (paths: string[], connectionId?: string | null) => void
   beginPendingImageAttachment: (previewUrl?: string) => string | null
   resolvePendingImageAttachment: (id: string, path: string, connectionId?: string | null) => void
+  revealPendingImageAttachment: (id: string, previewUrl?: string) => void
   dropPendingImageAttachment: (id: string) => void
   insertTypedText: (text: string) => boolean
   setNotice: (notice: string | null) => void
@@ -134,8 +142,9 @@ async function renderProbe(args: {
           disabled,
           resolveAttachmentOwner: args.resolveAttachmentOwner,
           attachResolvedPaths: args.attachResolvedPaths ?? (() => {}),
-          beginPendingImageAttachment: store.begin,
+          beginPendingImageAttachment: args.agent === 'omp' ? () => null : store.begin,
           resolvePendingImageAttachment: store.resolve,
+          revealPendingImageAttachment: store.reveal,
           dropPendingImageAttachment: store.drop,
           insertTypedText: args.insertTypedText ?? (() => true),
           setNotice: args.setNotice ?? (() => {}),
@@ -175,7 +184,7 @@ beforeEach(() => {
   vi.resetAllMocks()
   mocks.readClipboardText.mockResolvedValue('')
   mocks.readClipboardImageThumbnail.mockResolvedValue(null)
-  mocks.clipboardHasImage.mockResolvedValue(false)
+  mocks.clipboardHasImage.mockResolvedValue(true)
   mocks.readClipboardFilePaths.mockResolvedValue([])
   mocks.saveClipboardImageAsTempFile.mockResolvedValue(null)
 })
@@ -260,11 +269,7 @@ describe('useNativeChatComposerPaste', () => {
         }
       })
       expect(mocks.saveClipboardImageAsTempFile).toHaveBeenCalledWith({ connectionId: 'conn-1' })
-      if (source === 'event') {
-        expect(store.chips[0]?.path).toBe('/remote/tmp/omp.png')
-      } else {
-        expect(attachResolvedPaths).toHaveBeenCalledWith(['/remote/tmp/omp.png'], 'conn-1')
-      }
+      expect(attachResolvedPaths).toHaveBeenCalledWith(['/remote/tmp/omp.png'], 'conn-1')
       expect(setNotice.mock.calls.every(([notice]) => notice === null)).toBe(true)
     }
   )
@@ -389,7 +394,7 @@ describe('useNativeChatComposerPaste', () => {
     expect(store.chips[0]).toMatchObject({ path: '/tmp/orca-paste-2.png', pending: false })
   })
 
-  it('attaches directly when no clipboard preview was available', async () => {
+  it('settles the owned operation when no clipboard preview was available', async () => {
     mocks.readClipboardImageThumbnail.mockResolvedValue(null)
     mocks.saveClipboardImageAsTempFile.mockResolvedValue('C:\\Temp\\orca-paste-3.png')
     const store = createChipStore()
@@ -402,8 +407,8 @@ describe('useNativeChatComposerPaste', () => {
     await act(async () => {
       probe.latest().pasteFromClipboard()
     })
-    expect(store.chips).toHaveLength(0)
-    expect(attachResolvedPaths).toHaveBeenCalledWith(['C:\\Temp\\orca-paste-3.png'], null)
+    expect(store.chips[0]).toMatchObject({ path: 'C:\\Temp\\orca-paste-3.png', pending: false })
+    expect(attachResolvedPaths).not.toHaveBeenCalled()
   })
 
   it('inserts text independently of a failed image save', async () => {
@@ -425,8 +430,7 @@ describe('useNativeChatComposerPaste', () => {
   })
 
   it('still falls through to text when the clipboard holds no image', async () => {
-    mocks.readClipboardImageThumbnail.mockResolvedValue(null)
-    mocks.saveClipboardImageAsTempFile.mockResolvedValue(null)
+    mocks.clipboardHasImage.mockResolvedValue(false)
     mocks.readClipboardText.mockResolvedValue('hello')
     const insertTypedText = vi.fn()
     const store = createChipStore()
@@ -787,17 +791,21 @@ describe('file-manager copies', () => {
       mocks.saveClipboardImageAsTempFile.mockResolvedValue('/tmp/shot.png')
       const insertTypedText = vi.fn(() => true)
       const attachResolvedPaths = vi.fn()
+      const store = createChipStore()
       const probe = await renderProbe({
         resolveAttachmentOwner: () => ({ kind: 'local' }),
         insertTypedText,
-        attachResolvedPaths
+        attachResolvedPaths,
+        store
       })
       await act(async () => probe.latest().pasteFromClipboard())
       expect(insertTypedText).not.toHaveBeenCalled()
-      expect(attachResolvedPaths).toHaveBeenCalledExactlyOnceWith(['/tmp/shot.png'], null)
+      expect(store.chips[0]).toMatchObject({ path: '/tmp/shot.png', pending: false })
+      expect(attachResolvedPaths).not.toHaveBeenCalled()
     })
 
     it('types the label when no image came with the files', async () => {
+      mocks.clipboardHasImage.mockResolvedValue(false)
       mocks.readClipboardText.mockResolvedValue('notes.txt')
       mocks.readClipboardFilePaths.mockResolvedValue(['/Users/me/notes.txt'])
       const insertTypedText = vi.fn(() => true)
diff --git a/src/renderer/src/components/native-chat/use-native-chat-composer-paste.ts b/src/renderer/src/components/native-chat/use-native-chat-composer-paste.ts
index 1701c069b34..b9d5cc465cc 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-composer-paste.ts
+++ b/src/renderer/src/components/native-chat/use-native-chat-composer-paste.ts
@@ -3,7 +3,6 @@ import { useNativeChatPasteLifetime } from './use-native-chat-paste-lifetime'
 import { nativeChatAttachmentOwnerUnchanged } from './native-chat-resolved-path-ownership'
 import { assertClipboardTextWithinLimit } from '../../../../shared/clipboard-text'
 import { setNativeChatPasteFailure } from './native-chat-composer-notice'
-import type { AgentType } from '../../../../shared/agent-status-types'
 import { NATIVE_CHAT_CONTEXT_PASTE_MAX_BYTES } from './native-chat-composer-target'
 import { nativeChatPasteUnavailableNotice } from '@/lib/native-chat-paste-request'
 import {
@@ -22,33 +21,12 @@ import {
   saveNativeChatClipboardImage
 } from './native-chat-clipboard-image-save'
 
-export type UseNativeChatComposerPasteArgs = {
-  targetKey?: string
-  agent: AgentType
-  /** Live composer-disabled state (no pty / presence-lock); read at await-resume
-   *  via a ref so a flip mid-paste doesn't write into a guarded composer. */
-  disabled: boolean
-  caret: number
-  /** Resolved at paste time: SSH panes must save the clipboard image on the
-   *  remote host, or the attached path names a file the agent cannot read. */
-  resolveAttachmentOwner: () => NativeChatAttachmentOwner
-  attachResolvedPaths: (paths: string[], connectionId?: string | null) => void
-  beginPendingImageAttachment: (
-    previewUrl?: string,
-    pendingName?: string,
-    options?: { hidden?: true }
-  ) => string | null
-  resolvePendingImageAttachment: (id: string, path: string, connectionId?: string | null) => void
-  /** Shows a chip begun hidden, with its thumbnail. */
-  revealPendingImageAttachment?: (id: string, previewUrl?: string) => void
-  dropPendingImageAttachment: (id: string) => void
-  insertTypedText: (text: string) => boolean
-  setCaret: (caret: number) => void
-  setNotice: (notice: string | null, errorText?: string) => void
-}
+import type { UseNativeChatComposerPasteArgs } from './native-chat-composer-paste-options'
+export type { UseNativeChatComposerPasteArgs } from './native-chat-composer-paste-options'
 
 export function useNativeChatComposerPaste({
   targetKey,
+  attachmentScopeKey,
   disabled,
   caret,
   resolveAttachmentOwner,
@@ -71,6 +49,7 @@ export function useNativeChatComposerPaste({
   const { lifetime, track, startImageChip, keepStoreUploadAfterUnmount } =
     useNativeChatPasteLifetime({
       targetKey,
+      attachmentScopeKey,
       beginPendingImageAttachment,
       resolvePendingImageAttachment,
       revealPendingImageAttachment,
@@ -83,6 +62,15 @@ export function useNativeChatComposerPaste({
       setNotice(nativeChatPasteUnavailableNotice())
     }
   }, [lifetime, setNotice])
+  const dropImagePaste = useCallback(
+    (pendingId: string | null) => {
+      if (pendingId) {
+        lifetime.pending.delete(pendingId)
+        dropPendingImageAttachment(pendingId)
+      }
+    },
+    [lifetime, dropPendingImageAttachment]
+  )
 
   // Image failures do not decide whether text can be inserted. Beside pasted text, a server too old
   // to store the image drops only the image rendition, as an owner that takes no images does.
@@ -112,15 +100,11 @@ export function useNativeChatComposerPaste({
     [canPaste, setNotice]
   )
 
-  /** Settle the chip started at paste time, or attach directly when the paste
-   *  produced no placeholder (no clipboard preview was available). */
+  /** Settle the operation started at paste time, or attach directly if chips are unavailable. */
   const settleImagePaste = useCallback(
     (pendingId: string | null, path: string, originalOwner: NativeChatAttachmentOwner) => {
       if (!nativeChatAttachmentOwnerUnchanged(originalOwner, resolveAttachmentOwner())) {
-        if (pendingId) {
-          lifetime.pending.delete(pendingId)
-          dropPendingImageAttachment(pendingId)
-        }
+        dropImagePaste(pendingId)
         setNotice(nativeChatWorktreeNotReadyNotice())
         return
       }
@@ -135,7 +119,7 @@ export function useNativeChatComposerPaste({
     [
       attachResolvedPaths,
       lifetime,
-      dropPendingImageAttachment,
+      dropImagePaste,
       resolveAttachmentOwner,
       resolvePendingImageAttachment,
       setNotice
@@ -185,28 +169,23 @@ export function useNativeChatComposerPaste({
       // Why: snapshot the caret before the async temp-file round-trip — `caret`
       // state can move (further typing/selection) while the await is in flight.
       const caretAtPaste = caret
-      // Beside pasted text, a server too old to store the image drops it quietly, so its chip stays
-      // out of sight until the server answers; Send waits for it from the start all the same.
+      // Wait for server acceptance before minting a preview; the operation is visible from the start.
       const awaitServer = Boolean(text) && owner.kind === 'runtime-session'
-      const chip = startImageChip(owner, imageFile, {
-        hidden: awaitServer,
+      const { id: pendingId, reveal } = startImageChip(owner, imageFile, {
+        deferPreview: awaitServer,
         canShow: () => ownerAcceptsClipboardImage(owner) && canPaste()
       })
-      const pendingId = chip.id
       void (async () => {
         const saved = await saveClipboardImageForOwner(
           owner,
           async () => Boolean(text),
-          awaitServer ? chip.reveal : undefined
+          awaitServer ? reveal : undefined
         )
         if (keepStoreUploadAfterUnmount(pendingId, saved)) {
           return
         }
         if (saved.status !== 'saved' || !canPaste()) {
-          if (pendingId) {
-            lifetime.pending.delete(pendingId)
-            dropPendingImageAttachment(pendingId)
-          }
+          dropImagePaste(pendingId)
           return
         }
         settleImagePaste(pendingId, saved.tempPath, owner)
@@ -217,9 +196,8 @@ export function useNativeChatComposerPaste({
     },
     [
       canPaste,
-      lifetime,
       caret,
-      dropPendingImageAttachment,
+      dropImagePaste,
       insertTypedText,
       showPasteUnavailable,
       resolveAttachmentOwner,
@@ -278,26 +256,44 @@ export function useNativeChatComposerPaste({
         }
         return
       }
-      const thumbnailPromise = window.api.ui.readClipboardImageThumbnail().catch(() => null)
-      const savePromise = saveClipboardImageForOwner(owner, async () => {
+      const hasImage = await window.api.ui.clipboardHasImage().catch((error) => {
+        if (canPaste()) {
+          setNativeChatPasteFailure(setNotice, error)
+        }
+        return null
+      })
+      if (hasImage !== true) {
+        const read = await textRead
+        if (read?.labelsFiles) {
+          insertText(read.text)
+        }
+        return
+      }
+      if (!canPaste()) {
+        return
+      }
+      // Ownership starts before saving; a thumbnail only supplies its preview.
+      const pendingId = beginPendingImageAttachment()
+      if (pendingId) {
+        track(pendingId, '', owner)
+      }
+      void window.api.ui
+        .readClipboardImageThumbnail()
+        .catch(() => null)
+        .then((thumbnail) => {
+          if (pendingId && thumbnail) {
+            revealPendingImageAttachment?.(pendingId, thumbnail.dataUrl)
+          }
+        })
+      const saved = await saveClipboardImageForOwner(owner, async () => {
         const read = await textRead
         return Boolean(read?.text) && read?.labelsFiles !== true
       })
-      const thumbnail = await thumbnailPromise
-      const pendingId =
-        thumbnail && canPaste() ? beginPendingImageAttachment(thumbnail.dataUrl) : null
-      if (pendingId) {
-        track(pendingId, thumbnail?.dataUrl ?? '', owner)
-      }
-      const saved = await savePromise
       if (keepStoreUploadAfterUnmount(pendingId, saved)) {
         return
       }
       if (!canPaste() || saved.status !== 'saved') {
-        if (pendingId) {
-          lifetime.pending.delete(pendingId)
-          dropPendingImageAttachment(pendingId)
-        }
+        dropImagePaste(pendingId)
         // A file's label is typed only when no image came with it.
         const read = saved.status === 'empty' ? await textRead : null
         if (read?.labelsFiles) {
@@ -309,9 +305,9 @@ export function useNativeChatComposerPaste({
     })()
   }, [
     beginPendingImageAttachment,
+    revealPendingImageAttachment,
     canPaste,
-    lifetime,
-    dropPendingImageAttachment,
+    dropImagePaste,
     insertTypedText,
     keepStoreUploadAfterUnmount,
     track,
diff --git a/src/renderer/src/components/native-chat/use-native-chat-external-attachments.test.tsx b/src/renderer/src/components/native-chat/use-native-chat-external-attachments.test.tsx
index 74d257e5af1..f92095aaad1 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-external-attachments.test.tsx
+++ b/src/renderer/src/components/native-chat/use-native-chat-external-attachments.test.tsx
@@ -587,9 +587,9 @@ describe('useNativeChatExternalAttachments', () => {
         '/srv/agent-session-attachments/u1/shot.png',
         null
       )
-      expect(chips.drop).toHaveBeenCalledExactlyOnceWith('chip-2')
+      expect(chips.drop).not.toHaveBeenCalled()
       expect(chips.attachReferences).toHaveBeenCalledExactlyOnceWith([
-        '/srv/agent-session-attachments/u2/notes.md'
+        { id: 'chip-2', path: '/srv/agent-session-attachments/u2/notes.md' }
       ])
       // The client never reads its own disk for these paths: the server stores the bytes.
       expect(mocks.stat).not.toHaveBeenCalled()
@@ -653,11 +653,11 @@ describe('useNativeChatExternalAttachments', () => {
         )
       )
       expect(chips.attachReferences).toHaveBeenCalledExactlyOnceWith([
-        '/srv/agent-session-attachments/u1/notes.md'
+        { id: 'chip-1', path: '/srv/agent-session-attachments/u1/notes.md' }
       ])
     })
 
-    it('does not insert a file whose chip the user removed while it uploaded', async () => {
+    it('keeps each file operation ID through reference settlement, including removed chips', async () => {
       const upload = deferred<AgentSessionAttachmentPathUploadResult>()
       mocks.uploadNativeChatSessionAttachmentPaths.mockReturnValueOnce(upload.promise)
       const chips = trackingChips()
@@ -681,7 +681,8 @@ describe('useNativeChatExternalAttachments', () => {
       )
 
       expect(chips.attachReferences).toHaveBeenCalledExactlyOnceWith([
-        '/srv/agent-session-attachments/u2/notes.md'
+        { id: 'chip-1', path: '/srv/agent-session-attachments/u1/report.pdf' },
+        { id: 'chip-2', path: '/srv/agent-session-attachments/u2/notes.md' }
       ])
     })
 
@@ -709,7 +710,7 @@ describe('useNativeChatExternalAttachments', () => {
 
       expect(chips.drop).toHaveBeenCalledWith('chip-1')
       expect(chips.attachReferences).toHaveBeenCalledExactlyOnceWith([
-        '/srv/agent-session-attachments/u2/notes.md'
+        { id: 'chip-2', path: '/srv/agent-session-attachments/u2/notes.md' }
       ])
       // The cause, the size limit here, rides in the same notice.
       expect(notices).toEqual([
diff --git a/src/renderer/src/components/native-chat/use-native-chat-menu-paste-lifetime.test.tsx b/src/renderer/src/components/native-chat/use-native-chat-menu-paste-lifetime.test.tsx
new file mode 100644
index 00000000000..cbfed516c27
--- /dev/null
+++ b/src/renderer/src/components/native-chat/use-native-chat-menu-paste-lifetime.test.tsx
@@ -0,0 +1,273 @@
+// @vitest-environment happy-dom
+import { createRef } from 'react'
+import { act, cleanup, renderHook } from '@testing-library/react'
+import { afterEach, beforeEach, expect, it, vi } from 'vitest'
+import { useNativeChatComposerPaste } from './use-native-chat-composer-paste'
+import { useNativeChatComposerAttachments } from './use-native-chat-composer-attachments'
+import type { NativeChatComposerInput } from './native-chat-composer-input'
+import type { NativeChatAttachmentOwner } from './native-chat-attachment-upload'
+import { nativeChatImageSendBlock } from './native-chat-image-reattach'
+import {
+  clearNativeChatComposerDraftsForTests,
+  hydrateNativeChatComposerDrafts,
+  nativeChatComposerDraftWritesSettled,
+  readNativeChatComposerDraft,
+  setNativeChatComposerDraftOwnerResolver,
+  updateNativeChatComposerDraft,
+  structuredAgentSessionDraftScopeKey as scope
+} from './native-chat-composer-draft-store'
+import {
+  createMemoryNativeChatComposerDraftStorage,
+  setNativeChatComposerDraftStorageForTests
+} from './native-chat-composer-draft-storage'
+import {
+  clearNativeChatPendingAttachmentsForTests,
+  dropNativeChatPendingAttachmentsOwnedBy,
+  nativeChatPendingAttachmentSnapshot
+} from './native-chat-pending-attachment-cache'
+
+let previousApi: typeof window.api
+const draftOwner = { workspaceId: 'folder-1', executionHostId: 'local' as const }
+beforeEach(async () => {
+  previousApi = window.api
+  setNativeChatComposerDraftStorageForTests(createMemoryNativeChatComposerDraftStorage())
+  await hydrateNativeChatComposerDrafts()
+  setNativeChatComposerDraftOwnerResolver(() => draftOwner)
+})
+afterEach(async () => {
+  vi.useRealTimers()
+  cleanup()
+  await nativeChatComposerDraftWritesSettled()
+  clearNativeChatPendingAttachmentsForTests()
+  clearNativeChatComposerDraftsForTests()
+  window.api = previousApi
+})
+
+async function fixture(
+  kind: 'local' | 'ssh',
+  acceptsImages = true,
+  source: 'menu' | 'event' = 'menu'
+) {
+  const save = Promise.withResolvers<string | null>()
+  const thumbnail = Promise.withResolvers<{
+    dataUrl: string
+    width: number
+    height: number
+  } | null>()
+  const owner: NativeChatAttachmentOwner =
+    kind === 'ssh'
+      ? {
+          kind: 'ssh',
+          connectionId: 'ssh-1',
+          worktreePath: '/remote/folder',
+          expectedExecutionHostId: 'ssh:ssh-1',
+          expectedSshTargetId: 'ssh-1',
+          expectedSshConnectionGeneration: 1
+        }
+      : { kind: 'local' }
+  const path =
+    kind === 'ssh'
+      ? '/tmp/orca-paste-1-image.png'
+      : '/local/native-chat-pastes/orca-paste-1-image.png'
+  const saveCall = vi.fn(() => save.promise)
+  Object.defineProperty(window, 'api', {
+    configurable: true,
+    writable: true,
+    value: {
+      ui: {
+        readClipboardText: async () => '',
+        readClipboardFilePaths: async () => [],
+        clipboardHasImage: async () => true,
+        readClipboardImageThumbnail: () => thumbnail.promise,
+        saveClipboardImageAsTempFile: saveCall
+      }
+    }
+  })
+  const input = createRef<NativeChatComposerInput>()
+  const view = renderHook(() => {
+    const attachments = useNativeChatComposerAttachments({
+      attachmentScopeKey: scope('menu'),
+      allowWithoutTarget: true,
+      acceptsImages,
+      caret: 0,
+      disabled: false,
+      isComposing: () => false,
+      resolveTarget: () => null,
+      textareaRef: input,
+      setCaret: () => {},
+      setDraft: (update) =>
+        updateNativeChatComposerDraft(
+          scope('menu'),
+          {
+            text: update(readNativeChatComposerDraft(scope('menu')).text)
+          },
+          'immediate'
+        ),
+      setNotice: () => {}
+    })
+    const paste = useNativeChatComposerPaste({
+      targetKey: 'menu',
+      attachmentScopeKey: scope('menu'),
+      agent: acceptsImages ? 'claude' : 'omp',
+      disabled: false,
+      caret: 0,
+      resolveAttachmentOwner: () => owner,
+      ...attachments,
+      insertTypedText: () => true,
+      setCaret: () => {},
+      setNotice: () => {}
+    })
+    return { paste, attachments }
+  })
+  await act(async () => {
+    if (source === 'menu') {
+      view.result.current.paste.pasteFromClipboard()
+    } else {
+      const data = new DataTransfer()
+      data.items.add(new File(['png'], 'image.png', { type: 'image/png' }))
+      view.result.current.paste.handlePaste(new ClipboardEvent('paste', { clipboardData: data }))
+    }
+  })
+  await vi.waitFor(() =>
+    expect(saveCall).toHaveBeenCalledExactlyOnceWith(
+      kind === 'ssh' ? { connectionId: 'ssh-1' } : { forNativeChatDraft: true }
+    )
+  )
+  return { view, save, thumbnail, path }
+}
+
+const referencePastes = [
+  { kind: 'local', source: 'menu' },
+  { kind: 'ssh', source: 'menu' },
+  { kind: 'local', source: 'event' },
+  { kind: 'ssh', source: 'event' }
+] as const
+
+it.each(
+  referencePastes.flatMap((paste) =>
+    [true, false].map((acceptsImages) => ({ ...paste, acceptsImages }))
+  )
+)(
+  'can abandon stalled $kind $source operations after reopen with acceptsImages=$acceptsImages',
+  async ({ kind, source, acceptsImages }) => {
+    vi.useFakeTimers({ toFake: ['setTimeout', 'clearTimeout', 'Date'] })
+    const { view, save, thumbnail, path } = await fixture(kind, acceptsImages, source)
+    view.unmount()
+    const reopened = renderHook(() =>
+      useNativeChatComposerAttachments({
+        attachmentScopeKey: scope('menu'),
+        acceptsImages,
+        allowWithoutTarget: true,
+        caret: 0,
+        disabled: false,
+        isComposing: () => false,
+        resolveTarget: () => null,
+        textareaRef: createRef<NativeChatComposerInput>(),
+        setCaret: () => {},
+        setDraft: () => {},
+        setNotice: () => {}
+      })
+    )
+    await act(async () => vi.advanceTimersByTimeAsync(24 * 60 * 60 * 1000))
+    expect(reopened.result.current.imageAttachments).toHaveLength(1)
+    expect(nativeChatImageSendBlock(reopened.result.current.imageAttachments).holdsSend).toBe(true)
+    const id = reopened.result.current.imageAttachments[0].id
+    await act(async () => reopened.result.current.removeImageAttachment(id))
+    expect(nativeChatImageSendBlock(reopened.result.current.imageAttachments).holdsSend).toBe(false)
+    await act(async () => save.resolve(path))
+    await act(async () =>
+      thumbnail.resolve({ dataUrl: 'data:image/png;base64,AA', width: 1, height: 1 })
+    )
+    expect(nativeChatPendingAttachmentSnapshot(scope('menu'))).toEqual([])
+    expect(readNativeChatComposerDraft(scope('menu')).images).toEqual([])
+    expect(readNativeChatComposerDraft(scope('menu')).text).toBe('')
+  }
+)
+it.each(referencePastes)(
+  'keeps a $kind $source paste as a reference after close',
+  async ({ kind, source }) => {
+    const { view, save, thumbnail, path } = await fixture(kind, false, source)
+    await act(async () =>
+      thumbnail.resolve({ dataUrl: 'data:image/png;base64,AA', width: 1, height: 1 })
+    )
+    expect(view.result.current.attachments.imageAttachments).toHaveLength(1)
+    view.unmount()
+    await act(async () => save.resolve(path))
+    expect(nativeChatPendingAttachmentSnapshot(scope('menu'))).toEqual([])
+    expect(readNativeChatComposerDraft(scope('menu')).text).toContain(path)
+    expect(readNativeChatComposerDraft(scope('menu')).images).toEqual([])
+  }
+)
+it.each(referencePastes)(
+  'keeps mounted $kind $source paste references without image chips',
+  async ({ kind, source }) => {
+    const { save, thumbnail, path } = await fixture(kind, false, source)
+    await act(async () => thumbnail.resolve(null))
+    await act(async () => save.resolve(path))
+    expect(readNativeChatComposerDraft(scope('menu')).text).toContain(path)
+    expect(readNativeChatComposerDraft(scope('menu')).images).toEqual([])
+  }
+)
+
+it.each(['local', 'ssh'] as const)(
+  'preserves menu %s uploads closed before a delayed or absent thumbnail',
+  async (kind) => {
+    let completed = 0
+    for (const preview of ['delayed', 'missing', 'present'] as const) {
+      const { view, save, thumbnail, path } = await fixture(kind)
+      if (preview !== 'delayed') {
+        await act(async () =>
+          thumbnail.resolve(
+            preview === 'present'
+              ? { dataUrl: 'data:image/png;base64,AA', width: 1, height: 1 }
+              : null
+          )
+        )
+      }
+      view.unmount()
+      await act(async () => save.resolve(path))
+      expect(nativeChatPendingAttachmentSnapshot(scope('menu'))).toEqual([])
+      expect(readNativeChatComposerDraft(scope('menu')).images).toHaveLength(++completed)
+      expect(readNativeChatComposerDraft(scope('menu')).images.at(-1)).toMatchObject({
+        path,
+        ...(kind === 'ssh' ? { connectionId: 'ssh-1' } : {})
+      })
+      // The save also settles when a thumbnail has not answered at all.
+      if (preview === 'delayed') {
+        await act(async () => thumbnail.resolve(null))
+      }
+    }
+  }
+)
+
+it.each(['local', 'ssh'] as const)(
+  'settles menu %s images without a thumbnail while mounted',
+  async (kind) => {
+    const { save, thumbnail, path } = await fixture(kind)
+    await act(async () => thumbnail.resolve(null))
+    await act(async () => save.resolve(path))
+    expect(readNativeChatComposerDraft(scope('menu')).images[0]).toMatchObject({ path })
+  }
+)
+
+it.each([true, false])(
+  'ends pending operations for acceptsImages=%s on removal, deletion or failure',
+  async (acceptsImages) => {
+    for (const end of ['remove', 'workspace', 'failure'] as const) {
+      const { view, save, thumbnail, path } = await fixture('local', acceptsImages)
+      if (end === 'remove') {
+        await act(async () => view.result.current.attachments.clearImageAttachments())
+      } else if (end === 'workspace') {
+        dropNativeChatPendingAttachmentsOwnedBy(draftOwner)
+      }
+      view.unmount()
+      await act(async () => save.resolve(end === 'failure' ? null : path))
+      await act(async () =>
+        thumbnail.resolve({ dataUrl: 'data:image/png;base64,AA', width: 1, height: 1 })
+      )
+      expect(nativeChatPendingAttachmentSnapshot(scope('menu'))).toEqual([])
+      expect(readNativeChatComposerDraft(scope('menu')).images).toEqual([])
+      expect(readNativeChatComposerDraft(scope('menu')).text).toBe('')
+    }
+  }
+)
diff --git a/src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.test.tsx b/src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.test.tsx
new file mode 100644
index 00000000000..59a8d22d0f9
--- /dev/null
+++ b/src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.test.tsx
@@ -0,0 +1,141 @@
+// @vitest-environment happy-dom
+import { cleanup, renderHook } from '@testing-library/react'
+import { afterEach, beforeEach, expect, it } from 'vitest'
+import { useNativeChatPasteLifetime } from './use-native-chat-paste-lifetime'
+import {
+  clearNativeChatComposerDraftsForTests,
+  hydrateNativeChatComposerDrafts,
+  nativeChatComposerDraftWritesSettled,
+  readNativeChatComposerDraft,
+  setNativeChatComposerDraftOwnerResolver,
+  structuredAgentSessionDraftScopeKey as scope
+} from './native-chat-composer-draft-store'
+import {
+  type NativeChatComposerDraftOwner,
+  createMemoryNativeChatComposerDraftStorage,
+  setNativeChatComposerDraftStorageForTests
+} from './native-chat-composer-draft-storage'
+import {
+  addNativeChatPendingAttachment,
+  clearNativeChatPendingAttachmentsForTests,
+  dropNativeChatPendingAttachmentsOwnedBy,
+  nativeChatPendingAttachmentSnapshot,
+  settleNativeChatPendingAttachment,
+  takeNativeChatPendingAttachment
+} from './native-chat-pending-attachment-cache'
+import type { NativeChatAttachmentOwner } from './native-chat-attachment-upload'
+
+const WORKSPACE: NativeChatComposerDraftOwner = {
+  workspaceId: 'workspace-1',
+  executionHostId: 'local'
+}
+const owners: NativeChatAttachmentOwner[] = [
+  { kind: 'local' },
+  {
+    kind: 'ssh',
+    connectionId: 'ssh-1',
+    worktreePath: '/remote/worktree',
+    expectedExecutionHostId: 'ssh:ssh-1',
+    expectedSshTargetId: 'ssh-1',
+    expectedSshConnectionGeneration: 1
+  },
+  { kind: 'runtime-session', environmentId: 'paired', sessionId: 'a', pairingRevision: 1 }
+]
+
+beforeEach(async () => {
+  setNativeChatComposerDraftStorageForTests(createMemoryNativeChatComposerDraftStorage())
+  await hydrateNativeChatComposerDrafts()
+  setNativeChatComposerDraftOwnerResolver(() => WORKSPACE)
+})
+afterEach(async () => {
+  cleanup()
+  await nativeChatComposerDraftWritesSettled()
+  clearNativeChatPendingAttachmentsForTests()
+  clearNativeChatComposerDraftsForTests()
+})
+
+function fixture(owner: NativeChatAttachmentOwner) {
+  const view = renderHook(
+    ({ draftScope }) =>
+      useNativeChatPasteLifetime({
+        targetKey: draftScope,
+        attachmentScopeKey: draftScope,
+        beginPendingImageAttachment: () => 'upload',
+        resolvePendingImageAttachment: (id, path, connectionId) => {
+          settleNativeChatPendingAttachment(draftScope, id, path, connectionId)
+        },
+        dropPendingImageAttachment: (id) => {
+          takeNativeChatPendingAttachment(draftScope, id)
+        }
+      }),
+    { initialProps: { draftScope: scope('a') } }
+  )
+  addNativeChatPendingAttachment(scope('a'), { id: 'upload', path: '', pending: true })
+  view.result.current.track('upload', '', owner)
+  return { view, lifetime: view.result.current }
+}
+
+it.each(owners)('keeps a $kind upload when its composer closes', (owner) => {
+  const { view, lifetime } = fixture(owner)
+  view.unmount()
+  expect(nativeChatPendingAttachmentSnapshot(scope('a'))).toHaveLength(1)
+  expect(
+    lifetime.keepStoreUploadAfterUnmount('upload', {
+      status: 'saved',
+      tempPath: '/stored/image.png'
+    })
+  ).toBe(true)
+  expect(nativeChatPendingAttachmentSnapshot(scope('a'))).toEqual([])
+  expect(readNativeChatComposerDraft(scope('a')).images).toEqual([
+    {
+      id: 'upload',
+      path: '/stored/image.png',
+      ...(owner.kind === 'ssh' ? { connectionId: 'ssh-1' } : {})
+    }
+  ])
+  expect(readNativeChatComposerDraft(scope('b')).images).toEqual([])
+})
+
+it.each(owners)('keeps a $kind upload with its original scope after a target switch', (owner) => {
+  const { view, lifetime } = fixture(owner)
+  view.rerender({ draftScope: scope('b') })
+  expect(
+    lifetime.keepStoreUploadAfterUnmount('upload', {
+      status: 'saved',
+      tempPath: '/stored/image.png'
+    })
+  ).toBe(true)
+  expect(readNativeChatComposerDraft(scope('a')).images).toHaveLength(1)
+  expect(readNativeChatComposerDraft(scope('b')).images).toEqual([])
+})
+
+it.each(owners)('does not settle a removed $kind upload', (owner) => {
+  const { view, lifetime } = fixture(owner)
+  takeNativeChatPendingAttachment(scope('a'), 'upload')
+  view.unmount()
+  lifetime.keepStoreUploadAfterUnmount('upload', { status: 'saved', tempPath: '/stored/image.png' })
+  expect(readNativeChatComposerDraft(scope('a')).images).toEqual([])
+})
+
+it.each(owners)('drops a failed $kind upload after teardown', (owner) => {
+  const { view, lifetime } = fixture(owner)
+  view.unmount()
+  expect(lifetime.keepStoreUploadAfterUnmount('upload', { status: 'error' })).toBe(true)
+  expect(nativeChatPendingAttachmentSnapshot(scope('a'))).toEqual([])
+  expect(readNativeChatComposerDraft(scope('a')).images).toEqual([])
+})
+
+it.each(owners)(
+  'does not recreate a draft after its workspace is removed during a $kind upload',
+  (owner) => {
+    const { view, lifetime } = fixture(owner)
+    view.unmount()
+    dropNativeChatPendingAttachmentsOwnedBy(WORKSPACE)
+    lifetime.keepStoreUploadAfterUnmount('upload', {
+      status: 'saved',
+      tempPath: '/stored/image.png'
+    })
+    expect(nativeChatPendingAttachmentSnapshot(scope('a'))).toEqual([])
+    expect(readNativeChatComposerDraft(scope('a')).images).toEqual([])
+  }
+)
diff --git a/src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.ts b/src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.ts
index f801303dab1..41ee0f68438 100644
--- a/src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.ts
+++ b/src/renderer/src/components/native-chat/use-native-chat-paste-lifetime.ts
@@ -1,19 +1,14 @@
 import { useCallback, useLayoutEffect, useMemo, useRef } from 'react'
 import type { NativeChatAttachmentOwner } from './native-chat-attachment-upload'
+import { nativeChatPendingAttachmentSnapshot } from './native-chat-pending-attachment-cache'
 
 /**
- * The pending chips of pastes this composer started, released when it unmounts or changes target.
- * A paste uploading into a paired server's store outlives the composer, which a prompt card
- * unmounts: its chip stays pending in the scope's attachment cache, where its result settles for
- * the composer's return (`native-chat-pending-attachment-cache.ts`).
+ * Preview URLs belong to this composer; pending uploads belong to the draft's attachment cache.
  */
 export function useNativeChatPasteLifetime(args: {
   targetKey?: string
-  beginPendingImageAttachment: (
-    previewUrl?: string,
-    pendingName?: string,
-    options?: { hidden?: true }
-  ) => string | null
+  attachmentScopeKey?: string
+  beginPendingImageAttachment: (previewUrl?: string, pendingName?: string) => string | null
   /** Files the result into the composer's scope even once this instance is unmounted. */
   resolvePendingImageAttachment: (id: string, path: string, connectionId?: string | null) => void
   revealPendingImageAttachment?: (id: string, previewUrl?: string) => void
@@ -21,19 +16,23 @@ export function useNativeChatPasteLifetime(args: {
 }): {
   lifetime: { active: boolean; pending: Map<string, string> }
   track: (pendingId: string, preview: string, owner: NativeChatAttachmentOwner) => void
-  /** A paste's chip, shown at once with the clipboard's own thumbnail, or held out of sight
-   *  (`hidden`) until `reveal`; `id` is null when the composer refused it. */
+  /** Register the visible operation; `reveal` supplies its preview once the host accepts it. */
   startImageChip: (
     owner: NativeChatAttachmentOwner,
     imageFile: Blob,
-    options: { hidden: boolean; canShow: () => boolean }
+    options: { deferPreview: boolean; canShow: () => boolean }
   ) => { id: string | null; reveal: () => void }
   keepStoreUploadAfterUnmount: (
     pendingId: string | null,
     saved: { status: string; tempPath?: string }
   ) => boolean
 } {
-  const { targetKey, beginPendingImageAttachment, revealPendingImageAttachment } = args
+  const {
+    targetKey,
+    attachmentScopeKey,
+    beginPendingImageAttachment,
+    revealPendingImageAttachment
+  } = args
   const { resolvePendingImageAttachment, dropPendingImageAttachment } = args
   const dropPendingRef = useRef(dropPendingImageAttachment)
   useLayoutEffect(() => {
@@ -42,11 +41,12 @@ export function useNativeChatPasteLifetime(args: {
   const lifetime = useMemo(
     () => ({
       targetKey,
+      attachmentScopeKey,
       active: false,
       pending: new Map<string, string>(),
-      storeUploads: new Set<string>()
+      uploads: new Map<string, NativeChatAttachmentOwner>()
     }),
-    [targetKey]
+    [attachmentScopeKey, targetKey]
   )
   useLayoutEffect(() => {
     lifetime.active = true
@@ -56,19 +56,23 @@ export function useNativeChatPasteLifetime(args: {
         if (preview.startsWith('blob:')) {
           URL.revokeObjectURL(preview)
         }
-        if (!lifetime.storeUploads.has(id)) {
+        if (
+          lifetime.uploads.get(id)?.kind !== 'runtime-session' &&
+          !(
+            attachmentScopeKey &&
+            nativeChatPendingAttachmentSnapshot(attachmentScopeKey).some((chip) => chip.id === id)
+          )
+        ) {
           dropPendingRef.current(id)
         }
       }
       lifetime.pending.clear()
     }
-  }, [lifetime])
+  }, [attachmentScopeKey, lifetime])
   const track = useCallback(
     (pendingId: string, preview: string, owner: NativeChatAttachmentOwner) => {
       lifetime.pending.set(pendingId, preview)
-      if (owner.kind === 'runtime-session') {
-        lifetime.storeUploads.add(pendingId)
-      }
+      lifetime.uploads.set(pendingId, owner)
     },
     [lifetime]
   )
@@ -76,16 +80,22 @@ export function useNativeChatPasteLifetime(args: {
     (
       owner: NativeChatAttachmentOwner,
       imageFile: Blob,
-      options: { hidden: boolean; canShow: () => boolean }
+      options: { deferPreview: boolean; canShow: () => boolean }
     ): { id: string | null; reveal: () => void } => {
-      if (options.hidden) {
-        const id = beginPendingImageAttachment(undefined, undefined, { hidden: true })
+      if (options.deferPreview) {
+        const id = beginPendingImageAttachment()
         if (id) {
           track(id, '', owner)
         }
         // Through the scope's cache, so it shows even in a composer that came back since.
         const reveal = (): void => {
-          if (!id) {
+          if (
+            !id ||
+            (attachmentScopeKey &&
+              !nativeChatPendingAttachmentSnapshot(attachmentScopeKey).some(
+                (chip) => chip.id === id
+              ))
+          ) {
             return
           }
           const previewUrl = lifetime.active ? URL.createObjectURL(imageFile) : undefined
@@ -108,21 +118,42 @@ export function useNativeChatPasteLifetime(args: {
       }
       return { id, reveal: () => {} }
     },
-    [beginPendingImageAttachment, lifetime, revealPendingImageAttachment, track]
+    [attachmentScopeKey, beginPendingImageAttachment, lifetime, revealPendingImageAttachment, track]
   )
   const keepStoreUploadAfterUnmount = useCallback(
     (pendingId: string | null, saved: { status: string; tempPath?: string }): boolean => {
-      if (!pendingId || lifetime.active || !lifetime.storeUploads.has(pendingId)) {
+      if (!pendingId || lifetime.active) {
+        if (pendingId) {
+          lifetime.uploads.delete(pendingId)
+        }
         return false
       }
+      const owner = lifetime.uploads.get(pendingId)
+      if (
+        owner?.kind !== 'runtime-session' &&
+        !(
+          attachmentScopeKey &&
+          nativeChatPendingAttachmentSnapshot(attachmentScopeKey).some(
+            (chip) => chip.id === pendingId
+          )
+        )
+      ) {
+        lifetime.uploads.delete(pendingId)
+        return false
+      }
+      lifetime.uploads.delete(pendingId)
       if (saved.status === 'saved' && saved.tempPath) {
-        resolvePendingImageAttachment(pendingId, saved.tempPath, null)
+        resolvePendingImageAttachment(
+          pendingId,
+          saved.tempPath,
+          owner?.kind === 'ssh' ? owner.connectionId : null
+        )
       } else {
         dropPendingImageAttachment(pendingId)
       }
       return true
     },
-    [dropPendingImageAttachment, lifetime, resolvePendingImageAttachment]
+    [attachmentScopeKey, dropPendingImageAttachment, lifetime, resolvePendingImageAttachment]
   )
   return { lifetime, track, startImageChip, keepStoreUploadAfterUnmount }
 }