diff --git a/src/main/native-chat/transcript-input-content.perf.test.ts b/src/main/native-chat/transcript-input-content.perf.test.ts
index f0b1f652f12..04c82cb2335 100644
--- a/src/main/native-chat/transcript-input-content.perf.test.ts
+++ b/src/main/native-chat/transcript-input-content.perf.test.ts
@@ -172,23 +172,30 @@ it.each([1000, 10000])('does no glue work on %i rows preceding live legacy bound
 })
 
 it.each([
-  [8, 'continue'],
-  [80, 'continue'],
-  [8, 'continue continue'],
-  [80, 'continue continue']
+  [8, 'continue', false],
+  [80, 'continue', false],
+  [8, 'continue continue', false],
+  [80, 'continue continue', false],
+  [8, 'continue continue', true],
+  [80, 'continue continue', true]
 ] as const)(
   'bounds allocation work for eight identical legacy sends across %i eligible rows of %s',
-  (rows, text) => {
+  (rows, text, image) => {
     const count = 8
     const pending: NativeChatPendingSend[] = Array.from({ length: count }, (_, index) => ({
       id: `same-${index}`,
-      text: 'continue',
+      text: image && index < 2 ? 'continue continue' : 'continue',
+      imagePaths: image && index === 0 ? ['/tmp/i.png'] : undefined,
       sentAt: 1
     }))
     const messages = [
       ...Array.from({ length: rows }, (_, index) => user(text, `same-row-${index}`)),
       { ...user('', 'reply'), role: 'assistant' as const }
     ]
+    if (image) {
+      const group = [pending[0], pending[2], pending[3]]
+      expect(visibleNativeChatPendingSends(group, [messages[0]])).toEqual([])
+    }
     const BaseMap = globalThis.Map
     let writes = 0
     let lookups = 0
@@ -211,8 +218,10 @@ it.each([
       expect(remaining).toEqual([])
       // Eight legal row alternatives per signature; each state assigns, requires or omits each send.
       const states = 3 ** count
-      const witnessesPerRow = 2 ** count - 1 + count
-      const maxAllocationWrites = count * states * (witnessesPerRow + 1)
+      const witnessesPerRow = (image ? 2 : 1) * (2 ** count - 1) + count
+      // This corpus has two exact-rank patterns and one advance pattern; each signature keeps at most P rows.
+      const exactPatterns = image ? 2 : 1
+      const maxAllocationWrites = count * exactPatterns * states * (witnessesPerRow + 1)
       expect(writes).toBeLessThanOrEqual(maxAllocationWrites + rows + 2 ** count)
       // Every candidate allocates before its next-state lookup, including candidates never written.
       expect(allocationLookups).toBeLessThanOrEqual(maxAllocationWrites + rows * count + 2 ** count)
diff --git a/src/main/native-chat/transcript-input-content.test.ts b/src/main/native-chat/transcript-input-content.test.ts
index cf6b7e01e42..5b5f02360dd 100644
--- a/src/main/native-chat/transcript-input-content.test.ts
+++ b/src/main/native-chat/transcript-input-content.test.ts
@@ -15,7 +15,6 @@ const pending: NativeChatPendingSend = {
   id: 'send',
   sourceAgent: 'codex',
   text: '  literal [Image #1]\nkeep  spaces\u0085here  ',
-  imagePaths: ['/tmp/one.png', '/tmp/two.png'],
   sentAt: 1
 }
 
@@ -83,19 +82,17 @@ function reconcile(payload: Record<string, unknown>, entry = pending) {
   return prunePendingSends([entry], prepareNativeChatMessages([user, answer], 'codex'))
 }
 
-it('settles exact submitted Codex text and ordered local images through source decoding and display preparation', () => {
-  const payload = {
-    message: '[Image #1] [Image #2]    literal [Image #1]\nkeep  spaceshere',
-    local_images: ['/tmp/one.png', '/tmp/two.png'],
-    images: []
-  }
-  expect(reconcile(payload)).toEqual([])
-  expect(reconcile({ ...payload, local_images: ['/tmp/two.png', '/tmp/one.png'] })).toEqual([
-    pending
-  ])
+it('settles exact submitted Codex text while retaining literal image markers and spacing', () => {
+  const payload = { message: 'literal [Image #1]\nkeep  spaceshere', local_images: [], images: [] }
+  const entry = { ...pending, text: 'literal [Image #1]\nkeep  spaces\u0085here' }
+  expect(reconcile(payload, entry)).toEqual([])
+  expect(reconcile({ ...payload, local_images: ['/tmp/one.png'] }, entry)).toEqual([entry])
   expect(
-    reconcile({ ...payload, message: payload.message.replace('keep  spaces', 'keep spaces') })
-  ).toEqual([pending])
+    reconcile(
+      { ...payload, message: payload.message.replace('keep  spaces', 'keep spaces') },
+      entry
+    )
+  ).toEqual([entry])
 })
 
 it('does not turn unaccounted file-backed attachments or literal-marker differences into text-only delivery', () => {
@@ -115,8 +112,7 @@ it('matches the complete submitted file-mention text without inventing attachmen
     id: 'mention',
     sourceAgent: 'omp',
     sentAt: 1,
-    text: '  caption\tline\nend  ',
-    imagePaths: ['/tmp/one image.png']
+    text: '@"/tmp/one image.png"   caption\tline\nend'
   }
   const readOmp = (extra: unknown[] = []) =>
     decodeOmpTranscriptLine(
@@ -235,7 +231,7 @@ it('does not allocate a recorded Codex response/completed pair to two sends', ()
   ).toEqual(['second'])
 })
 
-it('matches per-frame OpenCode caption trimming and C1 paste sanitization without normalizing short typed input', () => {
+it('matches OpenCode text trimming and C1 paste sanitization without normalizing short typed input', () => {
   const decode = (text: string, id = 'user') =>
     opencodeMessages(
       { id, role: 'user', timestamp: null },
@@ -251,19 +247,14 @@ it('matches per-frame OpenCode caption trimming and C1 paste sanitization withou
     blocks: []
   }
   const input: NativeChatPendingSend = {
-    id: 'image',
+    id: 'text',
     sourceAgent: 'opencode',
     text: '  alpha\n\u009b31mbeta\ngamma  ',
-    imagePaths: ['/tmp/a.png'],
     sentAt: 1
   }
-  expect(prunePendingSends([input], [decode('@/tmp/a.png alpha\nbeta\ngamma'), answer])).toEqual([])
-  expect(
-    prunePendingSends([input], [decode('@/tmp/a.png   alpha\nbeta\ngamma  '), answer])
-  ).toEqual([])
-  expect(prunePendingSends([input], [decode('@/tmp/a.png alpha beta gamma'), answer])).toEqual([
-    input
-  ])
+  expect(prunePendingSends([input], [decode('alpha\nbeta\ngamma'), answer])).toEqual([])
+  expect(prunePendingSends([input], [decode('  alpha\nbeta\ngamma  '), answer])).toEqual([])
+  expect(prunePendingSends([input], [decode('alpha beta gamma'), answer])).toEqual([input])
   const short = { ...input, id: 'short', text: `  ${'x'.repeat(160)}  `, imagePaths: [] }
   expect(prunePendingSends([short], [decode('x'.repeat(160)), answer])).toEqual([short])
   expect(prunePendingSends([short], [decode(`  ${'x'.repeat(160)}  `), answer])).toEqual([])
diff --git a/src/main/runtime/rpc/methods/native-chat/native-chat.test.ts b/src/main/runtime/rpc/methods/native-chat/native-chat.test.ts
index 9599a06485f..e925f35321c 100644
--- a/src/main/runtime/rpc/methods/native-chat/native-chat.test.ts
+++ b/src/main/runtime/rpc/methods/native-chat/native-chat.test.ts
@@ -186,7 +186,6 @@ describe('nativeChat.readSession clientKind truncation gating', () => {
       const pending = {
         id: 'pending',
         text,
-        imagePaths: images,
         sourceAgent: 'codex' as const,
         sentAt: 0
       }
diff --git a/src/main/runtime/terminal/input/terminal-agent-prompt-chat.ts b/src/main/runtime/terminal/input/terminal-agent-prompt-chat.ts
index 5389abe6ead..12ba03bc9b8 100644
--- a/src/main/runtime/terminal/input/terminal-agent-prompt-chat.ts
+++ b/src/main/runtime/terminal/input/terminal-agent-prompt-chat.ts
@@ -9,11 +9,8 @@ import {
   waitForAgentPromptPromise
 } from './agent-prompt-signals'
 import { AGENT_TUI_CLEAR_INPUT_MAX } from '../../../../shared/agent-launch/startup/agent-tui-input-clear'
-import { agentImagePastePath } from '../../../../shared/agent-image-paste-path'
-import { agentImagePasteWrites } from '../../../../shared/agent-image-paste'
 import {
   buildNativeChatPasteBytes,
-  buildNativeChatImagePasteBytes,
   NATIVE_CHAT_SUBMIT
 } from '../../../../shared/native-chat/input/native-chat-paste-bytes'
 import {
@@ -56,34 +53,14 @@ export abstract class OrcaRuntimeWithTerminalChatPrompt extends OrcaRuntimeWithW
     ) {
       return Promise.resolve(refused)
     }
-    const rawBytes =
-      Buffer.byteLength(prompt.text) +
-      (prompt.imagePaths ?? []).reduce(
-        (sum, path) => sum + Buffer.byteLength(JSON.stringify(path)) + 1,
-        0
-      )
-    if (rawBytes > TERMINAL_INPUT_MAX_BYTES || (!prompt.text && !prompt.imagePaths?.length)) {
+    const rawBytes = Buffer.byteLength(prompt.text)
+    if (rawBytes > TERMINAL_INPUT_MAX_BYTES || !prompt.text) {
       return Promise.resolve(refused)
     }
     const pty = this.ptysById.get(binding.ptyId)
     const agent = pty?.foregroundAgent ?? pty?.launchAgent ?? prompt.agent
-    const body = (prompt.imagePaths?.length ? prompt.text.trim().length : prompt.text.length)
-      ? buildNativeChatPasteBytes(prompt.text)
-      : ''
-    const frames = [
-      prompt.text,
-      AGENT_TUI_CLEAR_INPUT_MAX,
-      ...agentImagePasteWrites(
-        agent,
-        (prompt.imagePaths ?? []).map((path) =>
-          buildNativeChatImagePasteBytes(agentImagePastePath(agent, path))
-        ),
-        body.length > 0
-      )
-    ]
-    if (body) {
-      frames.push(body)
-    }
+    const body = buildNativeChatPasteBytes(prompt.text)
+    const frames = [prompt.text, AGENT_TUI_CLEAR_INPUT_MAX, body]
     const byteLength =
       rawBytes + frames.reduce((sum, frame) => sum + Buffer.byteLength(frame), 0) + 1
     const entry = this.promptInputs.admit(
@@ -175,31 +152,21 @@ export abstract class OrcaRuntimeWithTerminalChatPrompt extends OrcaRuntimeWithW
           const platform = this.getPtyWriteHostPlatform(binding.ptyId)
           await write(frames[1])
           const joined = agentPromptSubmitJoinsPasteFrame(agent)
-          for (let index = 2; index < frames.length; index++) {
-            const frame = frames[index]
-            const last = index === frames.length - 1
-            const gate =
-              last && !joined
-                ? this.createAgentPromptRenderGate(
-                    binding.ptyId,
-                    getTerminalPasteIngestMs(platform, Buffer.byteLength(frame)),
-                    scheduleText
-                  )
-                : null
-            try {
-              gate?.arm()
-              await write(frame + (last && joined ? NATIVE_CHAT_SUBMIT : ''))
-              if (gate) {
-                await waitForAgentPromptPromise(gate.wait(), entry.signal)
-              } else if (!last) {
-                await waitForAgentPromptDelay(
-                  300 + getTerminalPasteIngestMs(platform, Buffer.byteLength(frame)),
-                  entry.signal
-                )
-              }
-            } finally {
-              gate?.dispose()
+          const gate = joined
+            ? null
+            : this.createAgentPromptRenderGate(
+                binding.ptyId,
+                getTerminalPasteIngestMs(platform, Buffer.byteLength(frames[2])),
+                scheduleText
+              )
+          try {
+            gate?.arm()
+            await write(frames[2] + (joined ? NATIVE_CHAT_SUBMIT : ''))
+            if (gate) {
+              await waitForAgentPromptPromise(gate.wait(), entry.signal)
             }
+          } finally {
+            gate?.dispose()
           }
           if (!joined) {
             await waitForAgentPromptDelay(
diff --git a/src/renderer/src/components/native-chat/composer/submit/use-native-chat-pty-composer-send.test.tsx b/src/renderer/src/components/native-chat/composer/submit/use-native-chat-pty-composer-send.test.tsx
new file mode 100644
index 00000000000..d2906e262ee
--- /dev/null
+++ b/src/renderer/src/components/native-chat/composer/submit/use-native-chat-pty-composer-send.test.tsx
@@ -0,0 +1,95 @@
+// @vitest-environment happy-dom
+import { act, cleanup, renderHook } from '@testing-library/react'
+import { afterEach, beforeEach, expect, it, vi } from 'vitest'
+import { useNativeChatPtyComposerSend } from './use-native-chat-pty-composer-send'
+
+const mocks = vi.hoisted(() => ({ host: vi.fn(), image: vi.fn(), text: vi.fn() }))
+vi.mock('../../session/terminal/send/native-chat-host-prompt', () => ({
+  sendNativeChatHostPrompt: mocks.host
+}))
+vi.mock('../../session/terminal/send/native-chat-runtime-image-send', () => ({
+  sendNativeChatMessageWithImageAttachments: mocks.image
+}))
+vi.mock('../../session/terminal/send/native-chat-runtime-send', () => ({
+  sendNativeChatMessage: mocks.text,
+  sendNativeChatTypedCommand: vi.fn(),
+  submitNativeChatPrompt: vi.fn()
+}))
+vi.mock('../../drafts/native-chat-composer-draft-store', () => ({
+  readNativeChatComposerDraft: () => ({})
+}))
+vi.mock('../pickers/native-chat-agent-reference-send', () => ({
+  serializeNativeChatAgentReferences: (text: string) => text
+}))
+vi.mock('../../paste/native-chat-composer-pasted-text-references', () => ({
+  admitNativeChatPastedText: () => true,
+  resolveNativeChatPastedText: (_scope: string, text: string) => text
+}))
+vi.mock('../../drafts/native-chat-launch-draft-send', () => ({
+  resolveNativeChatLaunchDraftSend: () => ({ sendOptions: {} })
+}))
+vi.mock('../../telemetry/native-chat-telemetry', () => ({ emitNativeChatMessageSent: vi.fn() }))
+vi.mock('@/store/index', () => ({
+  useAppStore: { getState: () => ({ tabsByWorktree: {}, clearNativeChatLaunchDraft: vi.fn() }) }
+}))
+
+beforeEach(() => {
+  vi.clearAllMocks()
+  const handle = { cancel: vi.fn(), settleAfterMs: 0 }
+  mocks.host.mockReturnValue(handle)
+  mocks.image.mockReturnValue(handle)
+})
+afterEach(cleanup)
+
+function composer(draft: string) {
+  const optimistic = vi.fn(() => 'pending')
+  const hook = renderHook(() =>
+    useNativeChatPtyComposerSend({
+      agent: 'codex',
+      draft,
+      draftScopeKey: 'pane',
+      imageAttachments: [{ path: '/tmp/original.png' }],
+      disabled: false,
+      isDispatchingSessionOption: false,
+      launchDraftResolved: true,
+      resolveTarget: () => ({ ptyId: 'pty', paneKey: 'pane' }),
+      classifySend: () => 'chat',
+      onOptimisticSend: optimistic,
+      sessionOptionsSurface: null,
+      terminalTabId: 'tab',
+      trackPendingSend: vi.fn(),
+      setDraft: vi.fn(),
+      setCaret: vi.fn(),
+      clearSkillOrigin: vi.fn(),
+      clearImageAttachments: vi.fn(),
+      setNotice: vi.fn()
+    })
+  )
+  return { hook, optimistic }
+}
+
+it.each(['', 'caption', '/model'])(
+  'keeps image send %j on the shipped attachment writer',
+  (text) => {
+    const { hook, optimistic } = composer(text)
+    act(() => expect(hook.result.current()).toBe(true))
+    expect(mocks.image).toHaveBeenCalledWith('codex', 'pty', text, ['/tmp/original.png'], {})
+    expect(mocks.host).not.toHaveBeenCalled()
+    expect(optimistic).toHaveBeenCalledWith(text, ['/tmp/original.png'], false, undefined)
+  }
+)
+
+it('uses the retry attachments rather than the current draft to choose the writer', () => {
+  const { hook, optimistic } = composer('unsent draft')
+  act(() =>
+    expect(hook.result.current({ text: 'retry', imagePaths: ['/tmp/retry.png'] })).toBe(true)
+  )
+  expect(mocks.image).toHaveBeenCalledWith('codex', 'pty', 'retry', ['/tmp/retry.png'], {})
+  expect(mocks.host).not.toHaveBeenCalled()
+  expect(optimistic).toHaveBeenCalledWith('retry', ['/tmp/retry.png'], true, undefined)
+  act(() => expect(hook.result.current({ text: 'text retry' })).toBe(true))
+  expect(mocks.host).toHaveBeenCalledWith(
+    expect.objectContaining({ prompt: { agent: 'codex', text: 'text retry' } })
+  )
+  expect(optimistic).toHaveBeenLastCalledWith('text retry', [], true, 'codex')
+})
diff --git a/src/renderer/src/components/native-chat/composer/submit/use-native-chat-pty-composer-send.ts b/src/renderer/src/components/native-chat/composer/submit/use-native-chat-pty-composer-send.ts
index 2c8c82dc904..bf861f3bb10 100644
--- a/src/renderer/src/components/native-chat/composer/submit/use-native-chat-pty-composer-send.ts
+++ b/src/renderer/src/components/native-chat/composer/submit/use-native-chat-pty-composer-send.ts
@@ -123,14 +123,10 @@ export function useNativeChatPtyComposerSend(args: {
             }
           : launchSendOptions
       let pendingHandle: NativeChatSendHandle | null = null
-      let sourceEvidence = classification === 'chat' && isTuiAgent(args.agent)
+      let sourceEvidence =
+        classification === 'chat' && imagePaths.length === 0 && isTuiAgent(args.agent)
       const legacySend = (dispatchScope: NativeChatPtyDispatchScope) =>
-        imagePaths.length > 0
-          ? sendNativeChatMessageWithImageAttachments(args.agent, target.ptyId, text, imagePaths, {
-              ...sendOptions,
-              dispatchScope
-            })
-          : sendNativeChatMessage(target.ptyId, text, { ...sendOptions, dispatchScope })
+        sendNativeChatMessage(target.ptyId, text, { ...sendOptions, dispatchScope })
       // Why: slash-like text must not silently drop its attached images.
       if (sourceEvidence && isTuiAgent(args.agent)) {
         pendingHandle = sendNativeChatHostPrompt({
@@ -139,7 +135,7 @@ export function useNativeChatPtyComposerSend(args: {
           worktreeId:
             chatWorkspaceByTabId(useAppStore.getState().tabsByWorktree, args.terminalTabId) ??
             undefined,
-          prompt: { agent: args.agent, text, imagePaths },
+          prompt: { agent: args.agent, text },
           onLegacy: legacySend,
           onEvidenceMode: (source) => {
             sourceEvidence = source
diff --git a/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.test.ts b/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.test.ts
index b6309543222..a936aa4b5b2 100644
--- a/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.test.ts
+++ b/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.test.ts
@@ -18,7 +18,7 @@ import {
 
 const scope = { paneKey: 'test', agent: 'opencode' }
 const session = 'session'
-const full = '@/tmp/a.png   one\ntwo\nthree  '
+const full = 'one\ntwo\nthree'
 const caption = '  one\ntwo\nthree  '
 function row(text: string, id: string, transcriptOrder = 1): NativeChatMessage {
   return {
@@ -48,26 +48,128 @@ function send(id: string, text: string, imagePaths?: string[]): NativeChatPendin
 }
 beforeEach(() => clearPendingSendCacheForTests())
 
+it('replaces failed legacy captions without merging different source requests or image-only paths', () => {
+  const legacy = { id: 'old', text: 'look', imagePaths: ['/tmp/a.png'], sentAt: 1 }
+  appendPendingSendCache(scope, { ...legacy, delivery: 'rejected' })
+  appendPendingSendCache(scope, { ...legacy, id: 'live', text: 'neighbor' })
+  expect(
+    appendPendingSendCache(scope, { ...legacy, id: 'new', imagePaths: ['/tmp/b.png'] }).map(
+      (entry) => entry.id
+    )
+  ).toEqual(['live', 'new'])
+  writePendingSendCache(scope, [{ ...send('source', '  look  '), delivery: 'rejected' }])
+  expect(appendPendingSendCache(scope, legacy).map((entry) => entry.id)).toEqual(['source', 'old'])
+  expect(
+    appendPendingSendCache(scope, { ...legacy, id: 'raw', text: '  look  ', imagePaths: [] }).map(
+      (entry) => entry.id
+    )
+  ).toEqual(['old', 'raw'])
+  writePendingSendCache(scope, [{ ...legacy, text: '', delivery: 'rejected' }])
+  expect(
+    appendPendingSendCache(scope, {
+      ...legacy,
+      id: 'different',
+      text: '',
+      imagePaths: ['/tmp/b.png']
+    }).map((entry) => entry.id)
+  ).toEqual(['old', 'different'])
+  expect(
+    appendPendingSendCache(scope, { ...legacy, id: 'same', text: '' }).map((entry) => entry.id)
+  ).toEqual(['different', 'same'])
+})
+
+it.each([false, true])(
+  'keeps source and compound image claims in chronological order, image first: %s',
+  (imageFirst) => {
+    const source = send('source', 'a b')
+    const group = [
+      { ...send('image', 'a b', ['/tmp/a.png']), sourceAgent: undefined },
+      { ...send('a', 'a'), sourceAgent: undefined },
+      { ...send('b', 'b'), sourceAgent: undefined }
+    ]
+    const pending = imageFirst ? [...group, source] : [source, ...group]
+    const messages = [row('a b', 'x'), answer]
+    const remaining = prunePendingSends(pending, messages, session)
+    expect(remaining.map((entry) => entry.id)).toEqual(
+      imageFirst ? ['source'] : ['image', 'a', 'b']
+    )
+    writePendingSendCache(scope, remaining)
+    expect(
+      visibleNativeChatPendingSends(readPendingSendCache(scope), messages, session).map(
+        (entry) => entry.id
+      )
+    ).toEqual(imageFirst ? ['source'] : ['image', 'a', 'b'])
+    expect(
+      prunePendingSends(
+        readPendingSendCache(scope),
+        [...messages, row('a b', 'y', 10), { ...answer, id: 'later-answer', transcriptOrder: 11 }],
+        session
+      )
+    ).toEqual([])
+    expect(
+      prunePendingSends([{ ...source, text: 'a  b' }, group[0]], messages, session).map(
+        (entry) => entry.id
+      )
+    ).toEqual(['source'])
+  }
+)
+
+it.each(['a', 'b'])(
+  'retains compound member %s’s advance window through partial retirement and remount',
+  (survivor) => {
+    const image = {
+      ...send('image', 'a b', ['/tmp/a.png']),
+      sourceAgent: undefined,
+      afterMessageId: undefined
+    }
+    const a = {
+      ...send('a', 'a'),
+      sourceAgent: undefined,
+      afterMessageId: undefined,
+      sentAt: survivor === 'a' ? 2000 : 1000
+    }
+    const b = {
+      ...send('b', 'b'),
+      sourceAgent: undefined,
+      afterMessageId: undefined,
+      sentAt: survivor === 'b' ? 2000 : 1000
+    }
+    const x = { ...row('a b', 'x'), timestamp: 2001 }
+    const early = { ...answer, timestamp: 1500 }
+    const remaining = prunePendingSends([image, a, b], [x, early], session)
+    expect(remaining.map((entry) => entry.id)).toEqual([survivor])
+    writePendingSendCache(scope, remaining)
+    const remounted = readPendingSendCache(scope)
+    expect(visibleNativeChatPendingSends(remounted, [], session)).toEqual([])
+    expect(prunePendingSends(remounted, [x, early], session).map((entry) => entry.id)).toEqual([
+      survivor
+    ])
+    expect(
+      prunePendingSends(remounted, [x, early, { ...answer, id: 'later', timestamp: 2002 }], session)
+    ).toEqual([])
+  }
+)
+
 it('keeps a spent overlapping source unit excluded through pruning, cache remount and paging', () => {
   appendPendingSendCache(scope, send('plain', full))
-  const pending = appendPendingSendCache(scope, send('image', caption, ['/tmp/a.png']))
+  const pending = appendPendingSendCache(scope, send('padded', caption))
   const receipt = row(full, 'shared')
   expect(
     visibleNativeChatPendingSends(pending, [receipt], session).map((entry) => entry.id)
-  ).toEqual(['image'])
+  ).toEqual(['padded'])
   writePendingSendCache(scope, prunePendingSends(pending, [receipt, answer], session))
   const remounted = readPendingSendCache(scope)
-  expect(remounted.map((entry) => entry.id)).toEqual(['image'])
+  expect(remounted.map((entry) => entry.id)).toEqual(['padded'])
   expect(prunePendingSends(remounted, [], session)).toBe(remounted)
   expect(
     visibleNativeChatPendingSends(remounted, [receipt, answer], session).map((entry) => entry.id)
-  ).toEqual(['image'])
+  ).toEqual(['padded'])
   expect(prunePendingSends(remounted, [receipt, row(full, 'new', 2), answer], session)).toEqual([])
   // An earlier unspent row first loaded later remains usable; the survivor's boundary was not advanced.
   expect(
     prunePendingSends(
       remounted,
-      [row('@/tmp/a.png one\ntwo\nthree', 'earlier', 0), receipt, answer],
+      [row('  one\ntwo\nthree  ', 'earlier', 0), receipt, answer],
       session
     )
   ).toEqual([])
diff --git a/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.ts b/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.ts
index e7a3a6a72fa..f8e2b886acf 100644
--- a/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.ts
+++ b/src/renderer/src/components/native-chat/session/terminal/delivery/native-chat-pending.ts
@@ -135,9 +135,15 @@ export function appendPendingSendCache(
   const requestKey = (input: NativeChatPendingSend) =>
     JSON.stringify([input.text, input.imagePaths ?? []])
   const contentKey = requestKey(entry)
+  const legacyKey = nativeChatPendingContentKey(entry)
   // Why: a resend replaces its failed copy; kept, that copy would claim the resend's row and pin it.
   const existing = readPendingSendCache(scope).filter(
-    (candidate) => !candidate.delivery || requestKey(candidate) !== contentKey
+    (candidate) =>
+      !candidate.delivery ||
+      (requestKey(candidate) !== contentKey &&
+        (candidate.sourceAgent ||
+          entry.sourceAgent ||
+          nativeChatPendingContentKey(candidate) !== legacyKey))
   )
   const owner = pendingSendCache.get(pendingSendScopeKey(scope))
   const boundary = owner?.boundary
diff --git a/src/renderer/src/components/native-chat/session/terminal/delivery/use-native-chat-pending-delivery.test.tsx b/src/renderer/src/components/native-chat/session/terminal/delivery/use-native-chat-pending-delivery.test.tsx
index eedc2b68878..345f7824600 100644
--- a/src/renderer/src/components/native-chat/session/terminal/delivery/use-native-chat-pending-delivery.test.tsx
+++ b/src/renderer/src/components/native-chat/session/terminal/delivery/use-native-chat-pending-delivery.test.tsx
@@ -360,34 +360,45 @@ it('assigns identical legacy occurrences at the real capability fallback and nev
   expect(remounted.result.current.pending).toEqual([])
 })
 
-it('transfers spent ownership to a reachable fallback glue witness, then retires its live dependencies', () => {
-  const first = mountOwned()
-  let source = '',
-    one = '',
-    two = ''
-  act(() => {
-    source = first.result.current.record('first second', undefined, false, 'opencode')
-    first.result.current.setSourceEvidence(source, true)
-    one = first.result.current.record('first', undefined, false, 'opencode')
-    two = first.result.current.record('second', undefined, false, 'opencode')
-  })
-  const x = sourceRow('first second', 'x')
-  first.rerender({ messages: [x] })
-  act(() => {
-    first.result.current.setSourceEvidence(one, false)
-    first.result.current.setSourceEvidence(two, false)
-  })
-  const messages = [x, { ...boundary, id: 'answer' }]
-  first.rerender({ messages })
-  expect(first.result.current.pending.map((entry) => entry.id)).toEqual([one, two])
-  first.unmount()
-  const remounted = mountOwned(messages)
-  expect(remounted.result.current.pending.map((entry) => entry.id)).toEqual([one, two])
-  remounted.rerender({
-    messages: [...messages, sourceRow('first second', 'y'), { ...boundary, id: 'answer-y' }]
-  })
-  expect(remounted.result.current.pending).toEqual([])
-})
+it.each([false, true])(
+  'transfers spent ownership to reachable fallback legacy proof, image member: %s',
+  (image) => {
+    const first = mountOwned()
+    let source = '',
+      attachment = '',
+      one = '',
+      two = ''
+    act(() => {
+      source = first.result.current.record('first second', undefined, false, 'opencode')
+      first.result.current.setSourceEvidence(source, true)
+      if (image) {
+        attachment = first.result.current.record('first second', ['/tmp/image.png'], false)
+      }
+      one = first.result.current.record('first', undefined, false, 'opencode')
+      two = first.result.current.record('second', undefined, false, 'opencode')
+    })
+    const x = sourceRow('first second', 'x')
+    first.rerender({ messages: [x] })
+    act(() => {
+      first.result.current.setSourceEvidence(one, false)
+      first.result.current.setSourceEvidence(two, false)
+    })
+    const messages = [x, { ...boundary, id: 'answer' }]
+    first.rerender({ messages })
+    expect(first.result.current.pending.map((entry) => entry.id)).toEqual(
+      image ? [attachment, one, two] : [one, two]
+    )
+    first.unmount()
+    const remounted = mountOwned(messages)
+    expect(remounted.result.current.pending.map((entry) => entry.id)).toEqual(
+      image ? [attachment, one, two] : [one, two]
+    )
+    remounted.rerender({
+      messages: [...messages, sourceRow('first second', 'y'), { ...boundary, id: 'answer-y' }]
+    })
+    expect(remounted.result.current.pending).toEqual([])
+  }
+)
 
 it('releases dead fallback group dependencies and does not accumulate receipts behind an incompatible draft', () => {
   const mounted = mountOwned()
diff --git a/src/renderer/src/components/native-chat/session/terminal/send/native-chat-host-prompt.ts b/src/renderer/src/components/native-chat/session/terminal/send/native-chat-host-prompt.ts
index 467667f05a8..71f54eec28e 100644
--- a/src/renderer/src/components/native-chat/session/terminal/send/native-chat-host-prompt.ts
+++ b/src/renderer/src/components/native-chat/session/terminal/send/native-chat-host-prompt.ts
@@ -40,12 +40,7 @@ export function sendNativeChatHostPrompt({
   onEvidenceMode: (source: boolean) => void
 }): NativeChatSendHandle {
   const deadline = performance.now() + OBSERVATION_MS
-  const bytes =
-    getTerminalInputByteLength(initialPrompt.text) +
-    (initialPrompt.imagePaths ?? []).reduce(
-      (sum, path) => sum + getTerminalInputByteLength(JSON.stringify(path)) + 1,
-      0
-    )
+  const bytes = getTerminalInputByteLength(initialPrompt.text)
   const reservation = reserveNativeChatPtyDispatch(ptyId, bytes)
   if (!reservation) {
     return {
diff --git a/src/renderer/src/components/native-chat/session/terminal/send/native-chat-runtime-image-send.ts b/src/renderer/src/components/native-chat/session/terminal/send/native-chat-runtime-image-send.ts
index 6549cdac10e..5ea6e251d27 100644
--- a/src/renderer/src/components/native-chat/session/terminal/send/native-chat-runtime-image-send.ts
+++ b/src/renderer/src/components/native-chat/session/terminal/send/native-chat-runtime-image-send.ts
@@ -94,7 +94,6 @@ export function sendNativeChatMessageWithImageAttachments(
       )
     },
     {
-      dispatchScope: options?.dispatchScope,
       onCancelUnsubmitted: () => clearUnsubmittedAgentInput(ptyId, options)
     }
   )
diff --git a/src/shared/native-chat/transcript/native-chat-input-content-key.ts b/src/shared/native-chat/transcript/native-chat-input-content-key.ts
index 828cfd4f664..0ef5a65cc70 100644
--- a/src/shared/native-chat/transcript/native-chat-input-content-key.ts
+++ b/src/shared/native-chat/transcript/native-chat-input-content-key.ts
@@ -4,8 +4,6 @@ import {
   type NativeChatSourcePending
 } from './native-chat-input-content'
 import { resolveNativeChatTranscriptAgent } from '../native-chat-agent-support'
-import { agentImagePastePath } from '../../agent-image-paste-path'
-import { getAgentImageHandling } from '../../agent-image-paste'
 import { buildNativeChatPasteBytes } from '../input/native-chat-paste-bytes'
 import {
   BRACKETED_PASTE_START,
@@ -44,9 +42,11 @@ function expectedSourceInput(pending: NativeChatSourcePending): ExpectedSourceIn
   if (cached) {
     return cached
   }
+  if (pending.imagePaths?.length) {
+    return { keys: [] }
+  }
   const provider = resolveNativeChatTranscriptAgent(pending.sourceAgent)
-  const paths = pending.imagePaths ?? []
-  let body = paths.length > 0 && !pending.text.trim() ? '' : submittedText(pending.text)
+  let body = submittedText(pending.text)
   if (
     provider === 'omp' &&
     buildNativeChatPasteBytes(pending.text).startsWith(BRACKETED_PASTE_START)
@@ -57,22 +57,6 @@ function expectedSourceInput(pending: NativeChatSourcePending): ExpectedSourceIn
     body = body.replace(/\r\n?/g, '\n')
   }
   let text = body
-  let images: readonly string[] = paths
-  if (getAgentImageHandling(pending.sourceAgent) !== 'attachment') {
-    text = [
-      ...paths.map((path) => {
-        const mention = agentImagePastePath(pending.sourceAgent, path)
-        return provider === 'omp' ? ompPastedText(mention) : mention
-      }),
-      ...(body ? [body] : [])
-    ].join(' ')
-    images = []
-  } else if (provider === 'codex') {
-    text =
-      paths.map((_, index) => `[Image #${index + 1}] `).join('') +
-      (paths.length && body ? ' ' : '') +
-      body
-  }
   if (provider === 'omp') {
     text = text.trim()
   }
@@ -86,27 +70,13 @@ function expectedSourceInput(pending: NativeChatSourcePending): ExpectedSourceIn
     text = rustTrim(text)
   }
   const texts =
-    provider === 'opencode'
-      ? [false, true].map((full) =>
-          [
-            ...paths.map((path) =>
-              opencodeFrame(submittedText(agentImagePastePath(pending.sourceAgent, path)), full)
-            ),
-            ...(body
-              ? [
-                  buildNativeChatPasteBytes(pending.text).startsWith(BRACKETED_PASTE_START)
-                    ? opencodeFrame(body, full)
-                    : body
-                ]
-              : [])
-          ].join(' ')
-        )
+    provider === 'opencode' &&
+    buildNativeChatPasteBytes(pending.text).startsWith(BRACKETED_PASTE_START)
+      ? [false, true].map((full) => opencodeFrame(body, full))
       : [text]
   const expected = {
     keys: [
-      ...new Set(
-        texts.map((value) => sourceKey(provider, nativeChatInputTextDigest(value), images))
-      )
+      ...new Set(texts.map((value) => sourceKey(provider, nativeChatInputTextDigest(value), [])))
     ]
   }
   pendingKeys.set(pending, expected)
diff --git a/src/shared/native-chat/transcript/native-chat-pending-reconciliation.ts b/src/shared/native-chat/transcript/native-chat-pending-reconciliation.ts
index 03e6f9c68f0..e7fc663e049 100644
--- a/src/shared/native-chat/transcript/native-chat-pending-reconciliation.ts
+++ b/src/shared/native-chat/transcript/native-chat-pending-reconciliation.ts
@@ -83,13 +83,17 @@ export function reconcileNativeChatPendingSends(
         members: [],
         proof: entry.receiptProof ?? 'source',
         glue: entry.receiptGlue,
+        glueMembers: new Set<number>(),
         advanced: new Set()
       }
       locked.set(key, witness)
     }
     witness.members.push(index)
+    if (entry.receiptGlue) {
+      witness.glueMembers!.add(index)
+    }
     witness.mask |= pendingReceiptBit(index, pending.length)
-    const eligible = nativeChatReceiptWindow(entry, snapshot, sessionId, witness.glue)
+    const eligible = nativeChatReceiptWindow(entry, snapshot, sessionId, entry.receiptGlue)
     if (
       witness.row.index >= 0 &&
       snapshot.rows.some(
@@ -229,7 +233,9 @@ export function commitNativeChatPendingReceipts<T extends NativeChatPendingSend>
       sourceReceipt: receipt,
       receiptMembers,
       receiptProof,
-      receiptGlue: witness?.glue ?? entry.receiptGlue,
+      receiptGlue: witness
+        ? (witness.glueMembers?.has(pending.indexOf(entry)) ?? witness.glue)
+        : entry.receiptGlue,
       receiptDependencies: applicable.length ? applicable : undefined
     }
   })
diff --git a/src/shared/native-chat/transcript/native-chat-pending-sends.test.ts b/src/shared/native-chat/transcript/native-chat-pending-sends.test.ts
index 64f92e7ec49..dc79742b6cf 100644
--- a/src/shared/native-chat/transcript/native-chat-pending-sends.test.ts
+++ b/src/shared/native-chat/transcript/native-chat-pending-sends.test.ts
@@ -42,6 +42,53 @@ function gluePending(id: string, text: string): NativeChatPendingSend {
   }
 }
 
+it('preserves legacy image caption matching followed by residual text on the same row', () => {
+  const pending = [
+    { ...gluePending('image', 'a b'), imagePaths: ['/tmp/a.png'] },
+    gluePending('a', 'a'),
+    gluePending('b', 'b')
+  ]
+  const row = userMessage('image-row', 'a b', 6000)
+  const messages = [GLUE_BOUNDARY, row]
+  expect(pendingSendsAsMessages(pending, messages)).toEqual([])
+  const retained = prunePendingSends(pending, messages)
+  expect(retained.map((entry) => entry.id)).toEqual(['image', 'a', 'b'])
+  expect(
+    prunePendingSends(retained, [...messages, assistantMessage('reply', 'done', 6100)])
+  ).toEqual([])
+})
+
+it('matches a legacy caption after the CLI echoes its attached file path', () => {
+  const pending = [{ ...gluePending('image', 'look'), imagePaths: ['/tmp/a.png'] }]
+  const messages = [
+    GLUE_BOUNDARY,
+    userMessage('image-row', '@/tmp/a.png look', 6000),
+    assistantMessage('reply', 'done', 6100)
+  ]
+  expect(prunePendingSends(pending, messages)).toEqual([])
+})
+
+it.each([false, true])(
+  'requires a real row before skipping an intervening legacy obligation, other row first: %s',
+  (first) => {
+    const pending = [
+      { ...gluePending('image', 'a b'), imagePaths: ['/tmp/a.png'] },
+      gluePending('other', 'z'),
+      gluePending('a', 'a'),
+      gluePending('b', 'b')
+    ]
+    const x = userMessage('x', 'a b', 6000)
+    const z = userMessage('z', 'z', 6000)
+    const answer = assistantMessage('reply', 'done', 6100)
+    expect(prunePendingSends(pending, [GLUE_BOUNDARY, x, answer]).map((entry) => entry.id)).toEqual(
+      ['other', 'a', 'b']
+    )
+    expect(
+      prunePendingSends(pending, [GLUE_BOUNDARY, ...(first ? [z, x] : [x, z]), answer])
+    ).toEqual([])
+  }
+)
+
 describe('glued rapid sends', () => {
   // Every send carries its own boundary, including later sends in a glued row.
   const mixedAgeGlue = (): { messages: NativeChatMessage[]; pending: NativeChatPendingSend[] } => {
diff --git a/src/shared/native-chat/transcript/native-chat-pending-witnesses.ts b/src/shared/native-chat/transcript/native-chat-pending-witnesses.ts
index 7c78803d0be..051e6d8c316 100644
--- a/src/shared/native-chat/transcript/native-chat-pending-witnesses.ts
+++ b/src/shared/native-chat/transcript/native-chat-pending-witnesses.ts
@@ -28,6 +28,7 @@ export type NativeChatPendingWitness = {
   requires: number
   proof: 'source' | 'legacy'
   glue?: boolean
+  glueMembers?: Set<number>
   advanced: Set<string>
 }
 
@@ -115,12 +116,14 @@ export function nativeChatPendingWitnesses(
     )
   )
   const candidates = new Map<string, NativeChatPendingWitness[]>()
+  const exactLegacyRows = new Map<number, Set<number>>()
   function offer(
     row: NativeChatReceiptRow,
     members: number[],
     proof: 'source' | 'legacy',
     requires = 0,
-    glue = false
+    glue = false,
+    glueMembers?: Set<number>
   ): void {
     if (options.onlyRows && !options.onlyRows.has(row.message.id)) {
       return
@@ -145,11 +148,27 @@ export function nativeChatPendingWitnesses(
       return
     }
     const mask = members.reduce((value, index) => value | pendingReceiptBit(index, count), 0)
-    const signature = `${proof}:${mask}:${requires}:${glue}`
+    const partition = glueMembers
+      ? members
+          .map(
+            (index) =>
+              `${index}:${glueMembers.has(index)}:${row.index < (glueMembers.has(index) ? lastGlueAdvance : lastAdvance)[index]}`
+          )
+          .join(',')
+      : ''
+    const signature = `${proof}:${mask}:${requires}:${glue}:${partition}`
     const alternatives = candidates.get(signature) ?? []
     if (alternatives.length >= count) {
       return
     }
+    const advanced = new Set(
+      members
+        .filter(
+          (index) =>
+            row.index < ((glueMembers?.has(index) ?? glue) ? lastGlueAdvance : lastAdvance)[index]
+        )
+        .map((index) => pending[index].id)
+    )
     alternatives.push({
       row,
       members,
@@ -157,11 +176,8 @@ export function nativeChatPendingWitnesses(
       requires,
       proof,
       glue,
-      advanced: new Set(
-        members
-          .filter((index) => row.index < (glue ? lastGlueAdvance : lastAdvance)[index])
-          .map((index) => pending[index].id)
-      )
+      glueMembers,
+      advanced
     })
     candidates.set(signature, alternatives)
   }
@@ -171,6 +187,7 @@ export function nativeChatPendingWitnesses(
       ? [{ entry: { ...entry, sourceAgent: undefined }, index }]
       : []
   )
+  const hasLegacyImages = legacy.some(({ entry }) => entry.imagePaths?.length)
   for (const [index, entry] of pending.entries()) {
     const projected = { ...entry, sourceAgent: undefined }
     const key = nativeChatPendingMatchKey(projected)
@@ -197,6 +214,11 @@ export function nativeChatPendingWitnesses(
         occurrence++
         // Qualify in the original stream, before spent ownership is subtracted.
         if (occurrence >= (entry.sourceAgent ? 1 : rank)) {
+          if (hasLegacyImages && pending[index].sourceReceipt?.sessionId !== sessionId) {
+            const exact = exactLegacyRows.get(row.index) ?? new Set<number>()
+            exact.add(index)
+            exactLegacyRows.set(row.index, exact)
+          }
           offer(row, [index], 'legacy')
         }
       }
@@ -222,6 +244,40 @@ export function nativeChatPendingWitnesses(
     }
     for (let residual = 1; residual < 1 << legacy.length; residual++) {
       const remaining = legacy.filter((_, index) => residual & (1 << index))
+      const requires = legacy.reduce(
+        (mask, member, index) =>
+          residual & (1 << index) ? mask : mask | pendingReceiptBit(member.index, count),
+        0
+      )
+      if (hasLegacyImages) {
+        const exact = remaining.filter(({ index }) => exactLegacyRows.get(row.index)?.has(index))
+        const rest = remaining.filter(({ index }) => !exactLegacyRows.get(row.index)?.has(index))
+        if (
+          exact.length &&
+          rest.length &&
+          remaining.some(({ entry }) => entry.imagePaths?.length)
+        ) {
+          const glued = selectPendingIndicesRepresentedByUserRows(
+            rest.map(({ entry }) => entry),
+            [
+              {
+                id: row.message.id,
+                text,
+                representablePendingIndices: new Set(
+                  rest.flatMap(({ index }, at) => (glueWindows[index](row) ? [at] : []))
+                )
+              }
+            ]
+          )
+          const glueMembers = new Set([...glued].map((at) => rest[at].index))
+          const members = remaining.flatMap(({ index }) =>
+            exactLegacyRows.get(row.index)?.has(index) || glueMembers.has(index) ? [index] : []
+          )
+          if (glueMembers.size && members.some((index) => pending[index].imagePaths?.length)) {
+            offer(row, members, 'legacy', requires, false, glueMembers)
+          }
+        }
+      }
       const represented = selectPendingIndicesRepresentedByUserRows(
         remaining.map(({ entry }) => entry),
         [
@@ -238,11 +294,6 @@ export function nativeChatPendingWitnesses(
         continue
       }
       const members = [...represented].map((at) => remaining[at].index)
-      const requires = legacy.reduce(
-        (mask, member, index) =>
-          residual & (1 << index) ? mask : mask | pendingReceiptBit(member.index, count),
-        0
-      )
       offer(row, members, 'legacy', requires, true)
     }
   }
diff --git a/src/shared/rpc-contract/terminal-chat-prompt-params.ts b/src/shared/rpc-contract/terminal-chat-prompt-params.ts
index c0178ba87d1..12386dd6bf1 100644
--- a/src/shared/rpc-contract/terminal-chat-prompt-params.ts
+++ b/src/shared/rpc-contract/terminal-chat-prompt-params.ts
@@ -5,15 +5,7 @@ import { isTuiAgent } from '../agent-launch/catalog/tui-agent-config'
 export const TerminalChatPromptParam = z
   .object({
     agent: z.custom<TuiAgent>(isTuiAgent),
-    text: z.string(),
-    imagePaths: z
-      .array(
-        z
-          .string()
-          .min(1)
-          .refine((path) => !path.includes('\0'))
-      )
-      .optional()
+    text: z.string()
   })
   .strict()
   .optional()
diff --git a/src/shared/runtime-terminal-send-contract.ts b/src/shared/runtime-terminal-send-contract.ts
index 8be427a5b1a..32c515dd838 100644
--- a/src/shared/runtime-terminal-send-contract.ts
+++ b/src/shared/runtime-terminal-send-contract.ts
@@ -1,7 +1,7 @@
 import type { WriteSettlement } from './terminal/pty/lifecycle/pty-write-settlement'
 import type { TuiAgent } from './agent-launch/catalog/tui-agent'
 
-export type TerminalChatPrompt = { agent: TuiAgent; text: string; imagePaths?: string[] }
+export type TerminalChatPrompt = { agent: TuiAgent; text: string }
 
 export type RuntimeTerminalSend = {
   handle: string