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
new file mode 100644
index 00000000000..144385e76e7
--- /dev/null
+++ b/src/renderer/src/components/native-chat/use-native-chat-composer-paste.test.tsx
@@ -0,0 +1,220 @@
+// @vitest-environment happy-dom
+import { afterEach, describe, expect, it, vi } from 'vitest'
+import { act } from 'react'
+import { createRoot, type Root } from 'react-dom/client'
+import { createElement } from 'react'
+import type { NativeChatAttachmentOwner } from './native-chat-attachment-upload'
+
+const mocks = vi.hoisted(() => ({
+  saveClipboardImageAsTempFile: vi.fn(),
+  readClipboardText: vi.fn()
+}))
+
+vi.mock('@/i18n/i18n', () => ({
+  translate: (_key: string, fallback: string) => fallback
+}))
+
+vi.mock('./native-chat-composer-target', () => ({
+  NATIVE_CHAT_CONTEXT_PASTE_MAX_BYTES: 1024
+}))
+
+vi.mock('./native-chat-attachment-upload', () => ({
+  nativeChatWorktreeNotReadyNotice: () => 'Worktree not ready — try again in a moment.'
+}))
+
+vi.stubGlobal('window', {
+  api: {
+    ui: {
+      saveClipboardImageAsTempFile: mocks.saveClipboardImageAsTempFile,
+      readClipboardText: mocks.readClipboardText
+    }
+  }
+})
+
+import { useNativeChatComposerPaste } from './use-native-chat-composer-paste'
+
+type HookApi = ReturnType<typeof useNativeChatComposerPaste>
+
+function Probe({
+  disabled,
+  resolveAttachmentOwner,
+  attachResolvedPaths,
+  insertTypedText,
+  setNotice,
+  onReady
+}: {
+  disabled: boolean
+  resolveAttachmentOwner: () => NativeChatAttachmentOwner
+  attachResolvedPaths: (paths: string[]) => void
+  insertTypedText: (text: string) => boolean
+  setNotice: (notice: string | null) => void
+  onReady: (api: HookApi) => void
+}): null {
+  onReady(
+    useNativeChatComposerPaste({
+      agent: 'claude',
+      disabled,
+      caret: 0,
+      resolveAttachmentOwner,
+      attachResolvedPaths,
+      insertTypedText,
+      setCaret: () => {},
+      setNotice
+    })
+  )
+  return null
+}
+
+let root: Root | null = null
+
+async function renderProbe(args: {
+  disabled?: boolean
+  resolveAttachmentOwner: () => NativeChatAttachmentOwner
+  attachResolvedPaths?: (paths: string[]) => void
+  insertTypedText?: (text: string) => boolean
+  setNotice?: (notice: string | null) => void
+}): Promise<{ latest: () => HookApi; setDisabled: (disabled: boolean) => Promise<void> }> {
+  const container = document.createElement('div')
+  document.body.append(container)
+  let api: HookApi | null = null
+  root = createRoot(container)
+  const render = async (disabled: boolean): Promise<void> => {
+    await act(async () => {
+      root?.render(
+        createElement(Probe, {
+          disabled,
+          resolveAttachmentOwner: args.resolveAttachmentOwner,
+          attachResolvedPaths: args.attachResolvedPaths ?? (() => {}),
+          insertTypedText: args.insertTypedText ?? (() => true),
+          setNotice: args.setNotice ?? (() => {}),
+          onReady: (next) => {
+            api = next
+          }
+        })
+      )
+    })
+  }
+  await render(args.disabled ?? false)
+  return {
+    latest: () => {
+      if (!api) {
+        throw new Error('Probe did not render')
+      }
+      return api
+    },
+    setDisabled: render
+  }
+}
+
+function imagePasteEvent(): {
+  clipboardData: DataTransfer
+  preventDefault: () => void
+  defaultPrevented: boolean
+} {
+  return {
+    clipboardData: { items: [{ type: 'image/png' }] } as unknown as DataTransfer,
+    preventDefault: vi.fn(),
+    defaultPrevented: false
+  }
+}
+
+const sshOwner: NativeChatAttachmentOwner = {
+  kind: 'ssh',
+  connectionId: 'conn-1',
+  worktreePath: '/remote/wt'
+}
+
+afterEach(() => {
+  root?.unmount()
+  root = null
+  vi.clearAllMocks()
+})
+
+describe('useNativeChatComposerPaste', () => {
+  it('surfaces a failed SSH image save through the composer notice', async () => {
+    mocks.saveClipboardImageAsTempFile.mockRejectedValue(
+      new Error('Remote connection dropped. Click Reconnect on the SSH target before retrying.')
+    )
+    const attachResolvedPaths = vi.fn()
+    const setNotice = vi.fn()
+    const probe = await renderProbe({
+      resolveAttachmentOwner: () => sshOwner,
+      attachResolvedPaths,
+      setNotice
+    })
+    await act(async () => {
+      probe.latest().handlePaste(imagePasteEvent())
+    })
+    expect(setNotice).toHaveBeenCalledWith(
+      'Remote connection dropped. Click Reconnect on the SSH target before retrying.'
+    )
+    expect(attachResolvedPaths).not.toHaveBeenCalled()
+  })
+
+  it('saves on the SSH host and attaches the returned remote path', async () => {
+    mocks.saveClipboardImageAsTempFile.mockResolvedValue('/remote/tmp/orca-paste-1.png')
+    const attachResolvedPaths = vi.fn()
+    const probe = await renderProbe({
+      resolveAttachmentOwner: () => sshOwner,
+      attachResolvedPaths
+    })
+    await act(async () => {
+      probe.latest().handlePaste(imagePasteEvent())
+    })
+    expect(mocks.saveClipboardImageAsTempFile).toHaveBeenCalledWith({ connectionId: 'conn-1' })
+    expect(attachResolvedPaths).toHaveBeenCalledWith(['/remote/tmp/orca-paste-1.png'])
+  })
+
+  it('stops pasteFromClipboard on a failed save instead of falling through to text', async () => {
+    mocks.saveClipboardImageAsTempFile.mockRejectedValue(new Error('sftp down'))
+    const insertTypedText = vi.fn()
+    const setNotice = vi.fn()
+    const probe = await renderProbe({
+      resolveAttachmentOwner: () => sshOwner,
+      insertTypedText,
+      setNotice
+    })
+    await act(async () => {
+      probe.latest().pasteFromClipboard()
+    })
+    expect(setNotice).toHaveBeenCalledWith('sftp down')
+    expect(mocks.readClipboardText).not.toHaveBeenCalled()
+    expect(insertTypedText).not.toHaveBeenCalled()
+  })
+
+  it('still falls through to text when the clipboard holds no image', async () => {
+    mocks.saveClipboardImageAsTempFile.mockResolvedValue(null)
+    mocks.readClipboardText.mockResolvedValue('hello')
+    const insertTypedText = vi.fn()
+    const probe = await renderProbe({
+      resolveAttachmentOwner: () => ({ kind: 'local' }),
+      insertTypedText
+    })
+    await act(async () => {
+      probe.latest().pasteFromClipboard()
+    })
+    expect(insertTypedText).toHaveBeenCalledWith('hello')
+  })
+
+  it('suppresses the failure notice when the composer became disabled mid-save', async () => {
+    let rejectSave: (error: Error) => void = () => {}
+    mocks.saveClipboardImageAsTempFile.mockReturnValue(
+      new Promise((_resolve, reject) => {
+        rejectSave = reject
+      })
+    )
+    const setNotice = vi.fn()
+    const probe = await renderProbe({
+      resolveAttachmentOwner: () => sshOwner,
+      setNotice
+    })
+    await act(async () => {
+      probe.latest().handlePaste(imagePasteEvent())
+    })
+    await probe.setDisabled(true)
+    await act(async () => {
+      rejectSave(new Error('sftp down'))
+    })
+    expect(setNotice).not.toHaveBeenCalled()
+  })
+})
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 b89909bcedc..dbb6a06ed03 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
@@ -1,5 +1,6 @@
 import { useCallback, useRef } from 'react'
 import { translate } from '@/i18n/i18n'
+import { extractIpcErrorMessage } from '@/lib/ipc-error'
 import type { AgentType } from '../../../../shared/agent-status-types'
 import { resolveImagePaste } from './native-chat-image-paste'
 import { NATIVE_CHAT_CONTEXT_PASTE_MAX_BYTES } from './native-chat-composer-target'
@@ -66,6 +67,36 @@ export function useNativeChatComposerPaste({
   const disabledRef = useRef(disabled)
   disabledRef.current = disabled
 
+  // Distinguishes 'empty' (no image on the clipboard — text may fall through)
+  // from 'failed' (save errored — the flow must stop and say why).
+  const saveClipboardImageForOwner = useCallback(
+    async (
+      owner: NativeChatAttachmentOwner
+    ): Promise<{ status: 'saved'; tempPath: string } | { status: 'empty' | 'failed' }> => {
+      try {
+        // SSH panes save the image on the remote host (SFTP) so the attached
+        // path is readable by the remote agent, matching terminal image paste.
+        const tempPath = await window.api.ui.saveClipboardImageAsTempFile(
+          owner.kind === 'ssh' ? { connectionId: owner.connectionId } : undefined
+        )
+        return tempPath ? { status: 'saved', tempPath } : { status: 'empty' }
+      } catch (error) {
+        // A failed save must be visible: over SSH it fails whenever the
+        // connection drops, and a silent no-op reads as a broken paste.
+        if (!disabledRef.current) {
+          setNotice(
+            extractIpcErrorMessage(
+              error,
+              translate('components.native-chat.composer.imagePasteFailed', 'Image paste failed.')
+            )
+          )
+        }
+        return { status: 'failed' }
+      }
+    },
+    [setNotice]
+  )
+
   const attachClipboardImageTempFile = useCallback(
     (tempPath: string) => {
       const result = resolveImagePaste(agent, tempPath)
@@ -108,21 +139,22 @@ export function useNativeChatComposerPaste({
       // state can move (further typing/selection) while the await is in flight.
       const caretAtPaste = caret
       void (async () => {
-        // SSH panes save the image on the remote host (SFTP) so the attached
-        // path is readable by the remote agent, matching terminal image paste.
-        const tempPath = await window.api.ui
-          .saveClipboardImageAsTempFile(
-            owner.kind === 'ssh' ? { connectionId: owner.connectionId } : undefined
-          )
-          .catch(() => null)
-        if (!tempPath || disabledRef.current) {
+        const saved = await saveClipboardImageForOwner(owner)
+        if (saved.status !== 'saved' || disabledRef.current) {
           return
         }
-        attachClipboardImageTempFile(tempPath)
+        attachClipboardImageTempFile(saved.tempPath)
         setCaret(caretAtPaste)
       })()
     },
-    [attachClipboardImageTempFile, caret, resolveAttachmentOwner, setCaret, setNotice]
+    [
+      attachClipboardImageTempFile,
+      caret,
+      resolveAttachmentOwner,
+      saveClipboardImageForOwner,
+      setCaret,
+      setNotice
+    ]
   )
 
   const pasteFromClipboard = useCallback(() => {
@@ -132,20 +164,16 @@ export function useNativeChatComposerPaste({
       // way to LEARN whether the clipboard holds an image. An image then gets
       // the not-ready notice (never a local-path attach for a possibly-remote
       // worktree); plain text falls through unaffected.
-      const tempPath = await window.api.ui
-        .saveClipboardImageAsTempFile(
-          owner.kind === 'ssh' ? { connectionId: owner.connectionId } : undefined
-        )
-        .catch(() => null)
-      if (disabledRef.current) {
+      const saved = await saveClipboardImageForOwner(owner)
+      if (disabledRef.current || saved.status === 'failed') {
         return
       }
-      if (tempPath) {
+      if (saved.status === 'saved') {
         if (owner.kind === 'not-ready') {
           setNotice(nativeChatWorktreeNotReadyNotice())
           return
         }
-        attachClipboardImageTempFile(tempPath)
+        attachClipboardImageTempFile(saved.tempPath)
         return
       }
       const text = await window.api.ui
@@ -158,7 +186,13 @@ export function useNativeChatComposerPaste({
         insertTypedText(text)
       }
     })()
-  }, [attachClipboardImageTempFile, insertTypedText, resolveAttachmentOwner, setNotice])
+  }, [
+    attachClipboardImageTempFile,
+    insertTypedText,
+    resolveAttachmentOwner,
+    saveClipboardImageForOwner,
+    setNotice
+  ])
 
   return { handlePaste, pasteFromClipboard }
 }
diff --git a/src/renderer/src/i18n/locales/en.json b/src/renderer/src/i18n/locales/en.json
index 76764b2aa6f..79bb974f1a9 100644
--- a/src/renderer/src/i18n/locales/en.json
+++ b/src/renderer/src/i18n/locales/en.json
@@ -12423,6 +12423,7 @@
         "localAttachmentUnsupported": "Local attachments are not available for remote sessions.",
         "removeAttachment": "Remove attachment",
         "pastedImageLabel": "Pasted image",
+        "imagePasteFailed": "Image paste failed.",
         "worktreeNotReady": "Worktree not ready — try again in a moment.",
         "uploadingAttachments": "Uploading {{value0}} file{{value1}} to remote…"
       },
diff --git a/src/renderer/src/i18n/locales/es.json b/src/renderer/src/i18n/locales/es.json
index 58ea5f6a80a..d2978db89c2 100644
--- a/src/renderer/src/i18n/locales/es.json
+++ b/src/renderer/src/i18n/locales/es.json
@@ -12423,6 +12423,7 @@
         "localAttachmentUnsupported": "Los archivos adjuntos locales no están disponibles para sesiones remotas.",
         "removeAttachment": "Quitar archivo adjunto",
         "pastedImageLabel": "Imagen pegada",
+        "imagePasteFailed": "Image paste failed.",
         "worktreeNotReady": "Worktree not ready — try again in a moment.",
         "uploadingAttachments": "Uploading {{value0}} file{{value1}} to remote…"
       },
diff --git a/src/renderer/src/i18n/locales/ja.json b/src/renderer/src/i18n/locales/ja.json
index 53efffc8cec..39085e01bc2 100644
--- a/src/renderer/src/i18n/locales/ja.json
+++ b/src/renderer/src/i18n/locales/ja.json
@@ -12423,6 +12423,7 @@
         "localAttachmentUnsupported": "ローカル添付ファイルはリモート セッションでは使用できません。",
         "removeAttachment": "添付ファイルを削除する",
         "pastedImageLabel": "貼り付けた画像",
+        "imagePasteFailed": "Image paste failed.",
         "worktreeNotReady": "Worktree not ready — try again in a moment.",
         "uploadingAttachments": "Uploading {{value0}} file{{value1}} to remote…"
       },
diff --git a/src/renderer/src/i18n/locales/ko.json b/src/renderer/src/i18n/locales/ko.json
index 2912cf1e1db..98ba88a10dd 100644
--- a/src/renderer/src/i18n/locales/ko.json
+++ b/src/renderer/src/i18n/locales/ko.json
@@ -12423,6 +12423,7 @@
         "localAttachmentUnsupported": "원격 세션에는 로컬 첨부 파일을 사용할 수 없습니다.",
         "removeAttachment": "첨부파일 삭제",
         "pastedImageLabel": "붙여넣은 이미지",
+        "imagePasteFailed": "Image paste failed.",
         "worktreeNotReady": "Worktree not ready — try again in a moment.",
         "uploadingAttachments": "Uploading {{value0}} file{{value1}} to remote…"
       },
diff --git a/src/renderer/src/i18n/locales/zh.json b/src/renderer/src/i18n/locales/zh.json
index ae2c8aa9c12..6e3296b14f3 100644
--- a/src/renderer/src/i18n/locales/zh.json
+++ b/src/renderer/src/i18n/locales/zh.json
@@ -12423,6 +12423,7 @@
         "localAttachmentUnsupported": "远程会话不支持本地附件。",
         "removeAttachment": "移除附件",
         "pastedImageLabel": "粘贴的图片",
+        "imagePasteFailed": "Image paste failed.",
         "worktreeNotReady": "Worktree not ready — try again in a moment.",
         "uploadingAttachments": "Uploading {{value0}} file{{value1}} to remote…"
       },