diff --git a/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.test.ts b/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.test.ts
index 991c6be217e..0003a0d2c34 100644
--- a/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.test.ts
+++ b/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.test.ts
@@ -51,6 +51,15 @@ describe('nativeChatSentPrompts', () => {
     expect(nativeChatSentPrompts({ messages, withoutImageMarkers: true })).toEqual([
       { id: '2', prompt: 'fix' }
     ])
+    // A marker the user typed, with no image of that number, is their text.
+    const typed = [
+      message('3', 'user', '[Image #1]'),
+      message('4', 'user', '', { blocks: [image, { type: 'text', text: 'not [Image #2]' }] })
+    ]
+    expect(nativeChatSentPrompts({ messages: typed, withoutImageMarkers: true })).toEqual([
+      { id: '3', prompt: '[Image #1]' },
+      { id: '4', prompt: 'not [Image #2]' }
+    ])
     // A terminal chat's transcript text is the agent's own, markers included.
     expect(nativeChatSentPrompts({ messages }).map(({ prompt }) => prompt)).toEqual([
       '[Image #1]',
diff --git a/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.ts b/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.ts
index ff34383ac52..f568168b647 100644
--- a/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.ts
+++ b/src/renderer/src/components/native-chat/native-chat-sent-prompt-history.ts
@@ -76,7 +76,15 @@ export function nativeChatSentPrompts(source: NativeChatRecallSource): NativeCha
       push(`command:${command.id}`, command.command)
     }
     const text = deriveNativeChatRowContent(message.blocks).markdown
-    push(message.id, source.withoutImageMarkers ? stripSentImagePromptMarkers(text) : text)
+    push(
+      message.id,
+      source.withoutImageMarkers
+        ? stripSentImagePromptMarkers(
+            text,
+            message.blocks.filter((block) => block.type === 'image-ref').length
+          )
+        : text
+    )
   }
   for (const command of commands.slice(nextCommand)) {
     push(`command:${command.id}`, command.command)
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.test.tsx b/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.test.tsx
index 8438c2b3445..35a0f60a50e 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.test.tsx
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.test.tsx
@@ -231,11 +231,18 @@ describe('inline queued editor', () => {
   })
 
   it('moves typing into the chat box without image markers, since the card keeps its images', async () => {
-    const hook = harness()
+    const withImage: AgentSessionQueuedMessage = {
+      ...message,
+      body: {
+        ...message.body,
+        blocks: [{ type: 'image-ref', path: '/tmp/a.png' }, ...message.body.blocks]
+      }
+    }
+    const hook = harness(true, { messages: [withImage] })
     await begin(hook)
-    act(() => hook.result.current.editor?.change('see [Image #1] again'))
+    act(() => hook.result.current.editor?.change('see [Image #1] not [Image #2]'))
     hook.rerender({ messages: [] })
-    expect(readNativeChatDraftCache(SCOPE)).toBe('see  again')
+    expect(readNativeChatDraftCache(SCOPE)).toBe('see  not [Image #2]')
   })
 
   it('a clean edit whose card leaves just closes; an unloaded list proves nothing', async () => {
diff --git a/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.ts b/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.ts
index f9b2b506068..7e44592eed8 100644
--- a/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.ts
+++ b/src/renderer/src/components/native-chat/use-structured-agent-session-queued-edit.ts
@@ -64,7 +64,13 @@ type Edit = {
 
 /** Unsaved typing goes to the chat box without the card's images, so no marker may name one. */
 function handOffEditText(edit: Edit): void {
-  appendNativeChatDraftCache(edit.draftKey, stripSentImagePromptMarkers(edit.text))
+  appendNativeChatDraftCache(
+    edit.draftKey,
+    stripSentImagePromptMarkers(
+      edit.text,
+      edit.body.blocks.filter((block) => block.type === 'image-ref').length
+    )
+  )
 }
 
 export function useStructuredAgentSessionQueuedEdit(args: {
diff --git a/src/shared/native-chat-image-transcript-markers.test.ts b/src/shared/native-chat-image-transcript-markers.test.ts
index 337a304e6d9..a88a1cf490e 100644
--- a/src/shared/native-chat-image-transcript-markers.test.ts
+++ b/src/shared/native-chat-image-transcript-markers.test.ts
@@ -316,6 +316,15 @@ describe('composer image chips at send and back', () => {
     ).toBe(`${chip('r-3')} then ${chip('r-1')}, not [Image #3]`)
   })
 
+  it('strips only the markers its images have, leaving a typed one past them', () => {
+    expect(stripSentImagePromptMarkers('[Image #1] then [Image #2], not [Image #3]', 2)).toBe(
+      'then , not [Image #3]'
+    )
+    expect(stripSentImagePromptMarkers('Explain the literal token [Image #1]', 0)).toBe(
+      'Explain the literal token [Image #1]'
+    )
+  })
+
   it('leaves a quoted file path that reads like a marker as typed, back or stripped', () => {
     const files = [
       formatNativeChatFileReference('/repo/[Image #1].md'),
@@ -326,7 +335,7 @@ describe('composer image chips at send and back', () => {
       expect(promptMarkersToImageReferences(`[Image #1] in ${file}`, ['r-1'])).toBe(
         `${chip('r-1')} in ${file}`
       )
-      expect(stripSentImagePromptMarkers(`[Image #1] in ${file} [Image #1]`)).toBe(`in ${file}`)
+      expect(stripSentImagePromptMarkers(`[Image #1] in ${file} [Image #1]`, 1)).toBe(`in ${file}`)
     }
   })
 
diff --git a/src/shared/native-chat-image-transcript-markers.ts b/src/shared/native-chat-image-transcript-markers.ts
index bc850c2404a..7c3b04fa2f5 100644
--- a/src/shared/native-chat-image-transcript-markers.ts
+++ b/src/shared/native-chat-image-transcript-markers.ts
@@ -86,11 +86,14 @@ export function promptMarkersToImageReferences(text: string, imageIds: readonly
   })
 }
 
-/** A structured chat's sent text without the `[Image #k]` markers its send added. */
-export function stripSentImagePromptMarkers(text: string): string {
+/** A structured chat's sent text without the `[Image #k]` markers its send added for its
+ *  `imageCount` images. A number past its images is left as typed. */
+export function stripSentImagePromptMarkers(text: string, imageCount: number): string {
   return withoutStrippedMarkerSpace(
     text,
-    replaceSentImagePromptMarkers(text, () => '')
+    replaceSentImagePromptMarkers(text, (number, marker) =>
+      number >= 1 && number <= imageCount ? '' : marker
+    )
   )
 }
 
diff --git a/src/shared/structured-agent-session-first-prompt.spec.ts b/src/shared/structured-agent-session-first-prompt.spec.ts
index 9b0c6d4a3c3..2bac3e6aae7 100644
--- a/src/shared/structured-agent-session-first-prompt.spec.ts
+++ b/src/shared/structured-agent-session-first-prompt.spec.ts
@@ -84,12 +84,31 @@ describe('first structured chat prompt', () => {
   })
 
   it('names a chat by what was asked, not by where its images sat', () => {
+    const withImages = (text: string, images: number, itemId: string) =>
+      message('', {
+        itemId,
+        body: {
+          kind: 'message',
+          role: 'user',
+          blocks: [
+            ...Array.from({ length: images }, () => ({
+              type: 'image-ref' as const,
+              path: '/tmp/a.png'
+            })),
+            { type: 'text', text }
+          ]
+        }
+      })
     expect(
       firstStructuredAgentSessionPrompt([
-        message('[Image #1] '),
-        message('compare [Image #1] with [Image #2]', { itemId: 'second' })
+        withImages('[Image #1] ', 1, 'first'),
+        withImages('compare [Image #1] with [Image #2]', 2, 'second')
       ])
     ).toBe('compare  with')
+    // A marker the user typed, with no image of that number, is their text.
+    expect(firstStructuredAgentSessionPrompt([message('Explain [Image #1]')])).toBe(
+      'Explain [Image #1]'
+    )
   })
 
   it('skips punctuation-only entries in favor of the first text request', () => {
diff --git a/src/shared/structured-agent-session-first-prompt.ts b/src/shared/structured-agent-session-first-prompt.ts
index 0c4c8fe90b1..1ef24ef5fbc 100644
--- a/src/shared/structured-agent-session-first-prompt.ts
+++ b/src/shared/structured-agent-session-first-prompt.ts
@@ -24,6 +24,7 @@ export function firstStructuredAgentSessionPrompt(
       continue
     }
     let prompt = ''
+    const imageCount = body.blocks.filter((block) => block.type === 'image-ref').length
     for (const block of body.blocks) {
       if (block.type === 'text') {
         if (prompt) {
@@ -31,7 +32,7 @@ export function firstStructuredAgentSessionPrompt(
         }
         // A title names what was asked; `[Image #N]` only says where an image sat.
         prompt += sliceAtCodeUnitLimit(
-          stripSentImagePromptMarkers(block.text),
+          stripSentImagePromptMarkers(block.text, imageCount),
           STRUCTURED_CHAT_NAME_PROMPT_LIMIT - prompt.length
         )
         if (prompt.length >= STRUCTURED_CHAT_NAME_PROMPT_LIMIT) {