diff --git a/src/renderer/src/components/native-chat/NativeChatComposerActions.test.tsx b/src/renderer/src/components/native-chat/NativeChatComposerActions.test.tsx
index ae315b4530a..ecffdbe9f94 100644
--- a/src/renderer/src/components/native-chat/NativeChatComposerActions.test.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatComposerActions.test.tsx
@@ -121,7 +121,7 @@ describe('NativeChatComposerActions', () => {
         attachDisabled={false}
         dictationDisabled={false}
         sendDisabled
-        sendBlockedReason="Attach the image again or remove it"
+        sendBlockedReason="An image couldn't be brought back. Remove it to send."
         isWorking={false}
         isDictating={false}
         isDictationHoldMode={false}
@@ -135,7 +135,9 @@ describe('NativeChatComposerActions', () => {
       />
     )
 
-    const send = screen.getByRole('button', { name: 'Attach the image again or remove it' })
+    const send = screen.getByRole('button', {
+      name: "An image couldn't be brought back. Remove it to send."
+    })
     expect(send.hasAttribute('disabled')).toBe(true)
   })
 })
diff --git a/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.test.tsx b/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.test.tsx
index e2ac63dda29..879c71bc991 100644
--- a/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.test.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.test.tsx
@@ -54,7 +54,7 @@ describe('NativeChatImageAttachmentPreview', () => {
     expect(mocks.useLocalImageSrc).toHaveBeenCalledWith(undefined, '', undefined)
   })
 
-  it('shows an image the draft could not keep as one to attach again, and lets it be removed', () => {
+  it('shows a pasted image that could not come back by name, says it was not kept, and lets it be removed', () => {
     mocks.useLocalImageSrc.mockReturnValue(undefined)
     const onRemove = vi.fn()
     vi.stubGlobal('IntersectionObserver', undefined)
@@ -67,10 +67,31 @@ describe('NativeChatImageAttachmentPreview', () => {
 
     expect(
       screen.getByRole('img', {
-        name: "Pasted image wasn't saved with this draft. Attach it again to send it."
+        name: "This pasted image couldn't be brought back with this draft. Remove it, and paste it again if you still need it."
       })
     ).toBeTruthy()
+    expect(screen.getByText('Pasted image')).toBeTruthy()
+    expect(screen.getByText('Not kept')).toBeTruthy()
     screen.getByRole('button', { name: 'Remove attachment' }).click()
     expect(onRemove).toHaveBeenCalledWith('m1')
   })
+
+  it('shows a file that could not come back by name, with a visible attach-again hint', () => {
+    mocks.useLocalImageSrc.mockReturnValue(undefined)
+    vi.stubGlobal('IntersectionObserver', undefined)
+    render(
+      <NativeChatImageAttachmentPreview
+        attachment={{ id: 'm2', path: '', unavailableName: 'diagram.png' }}
+        onRemove={vi.fn()}
+      />
+    )
+
+    expect(
+      screen.getByRole('img', {
+        name: "diagram.png couldn't be brought back with this draft. Attach it again or remove it."
+      })
+    ).toBeTruthy()
+    expect(screen.getByText('diagram.png')).toBeTruthy()
+    expect(screen.getByText('Attach again')).toBeTruthy()
+  })
 })
diff --git a/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.tsx b/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.tsx
index f27687af0c3..f1ce3d2c730 100644
--- a/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.tsx
+++ b/src/renderer/src/components/native-chat/NativeChatImageAttachmentPreview.tsx
@@ -51,7 +51,8 @@ function RemoveAttachmentButton({ onRemove }: { onRemove: () => void }): React.J
   )
 }
 
-/** An image the draft names but couldn't keep: it waits to be attached again, or removed. */
+/** An image the draft names but couldn't bring back. A file can be attached again in its place; a
+ *  pasted image can't be matched by a new paste, so its copy asks only for removal. */
 function NativeChatUnavailableImageChip({
   id,
   name,
@@ -61,20 +62,34 @@ function NativeChatUnavailableImageChip({
   name: string
   onRemove: (id: string) => void
 }): React.JSX.Element {
-  const explanation = translate(
-    'components.native-chat.composer.imageNotSavedWithDraft',
-    "{{name}} wasn't saved with this draft. Attach it again to send it.",
-    { name: attachmentLabel(name) }
-  )
+  const pasted = isNativeChatPastedImagePath(name)
+  const label = attachmentLabel(name)
+  const explanation = pasted
+    ? translate(
+        'components.native-chat.composer.pastedImageNotBroughtBack',
+        "This pasted image couldn't be brought back with this draft. Remove it, and paste it again if you still need it."
+      )
+    : translate(
+        'components.native-chat.composer.imageNotBroughtBack',
+        "{{name}} couldn't be brought back with this draft. Attach it again or remove it.",
+        { name: label }
+      )
+  const hint = pasted
+    ? translate('components.native-chat.composer.pastedImageNotKeptLabel', 'Not kept')
+    : translate('components.native-chat.composer.imageAttachAgainLabel', 'Attach again')
   return (
-    <div className="relative size-14 shrink-0">
+    <div className="relative h-14 max-w-40 shrink-0">
       <div
         role="img"
         aria-label={explanation}
         title={explanation}
-        className="flex size-full items-center justify-center rounded-md border border-dashed border-border bg-background"
+        className="flex h-full items-center gap-2 rounded-md border border-dashed border-border bg-background px-2"
       >
-        <ImageOff className="size-5 text-muted-foreground" />
+        <ImageOff className="size-4 shrink-0 text-muted-foreground" />
+        <div className="flex min-w-0 flex-col text-xs">
+          <span className="truncate text-foreground">{label}</span>
+          <span className="truncate text-muted-foreground">{hint}</span>
+        </div>
       </div>
       <RemoveAttachmentButton onRemove={() => onRemove(id)} />
     </div>
diff --git a/src/renderer/src/components/native-chat/native-chat-composer-draft-store.test.ts b/src/renderer/src/components/native-chat/native-chat-composer-draft-store.test.ts
index 6bf65ee8ab2..f8a7ec1f830 100644
--- a/src/renderer/src/components/native-chat/native-chat-composer-draft-store.test.ts
+++ b/src/renderer/src/components/native-chat/native-chat-composer-draft-store.test.ts
@@ -203,15 +203,37 @@ describe('native-chat composer draft store', () => {
     )
     const reloaded = await reload()
 
-    reloaded.attachments.appendNativeChatAttachmentCache('tab-1:pane', [
-      { id: 'again', path: '/Users/me/Desktop/shot.png' }
-    ])
+    reloaded.attachments.appendNativeChatAttachmentCache(
+      'tab-1:pane',
+      [{ id: 'again', path: '/Users/me/Desktop/shot.png' }],
+      { fromUser: true }
+    )
     expect(reloaded.attachments.readNativeChatAttachmentCache('tab-1:pane')).toEqual([
       { id: 'again', path: '/Users/me/Desktop/shot.png' },
       IMAGES[0]
     ])
   })
 
+  it('adds an image Stop gives back next to a placeholder with its name, never in its place', async () => {
+    storage.setItem(
+      `${DRAFT_KEY_PREFIX}${encodeURIComponent('tab-1:pane')}`,
+      JSON.stringify({
+        text: 'compare with this',
+        images: [{ id: 'm', path: '', unavailableName: 'image.png' }],
+        savedAt: 1
+      })
+    )
+    const reloaded = await reload()
+
+    reloaded.attachments.appendNativeChatAttachmentCache('tab-1:pane', [
+      { id: 'withdrawn-cm-1-1', path: '/Users/me/Downloads/image.png' }
+    ])
+    expect(reloaded.attachments.readNativeChatAttachmentCache('tab-1:pane')).toEqual([
+      { id: 'm', path: '', unavailableName: 'image.png' },
+      { id: 'withdrawn-cm-1-1', path: '/Users/me/Downloads/image.png' }
+    ])
+  })
+
   it('appends a given-back message after a draft restored from a reload', async () => {
     modules.drafts.writeNativeChatDraftCache('tab-1:pane', 'mine')
     modules.store.flushNativeChatComposerDrafts()
diff --git a/src/renderer/src/components/native-chat/native-chat-image-reattach.ts b/src/renderer/src/components/native-chat/native-chat-image-reattach.ts
index 3591eb3487e..29d35cf90e9 100644
--- a/src/renderer/src/components/native-chat/native-chat-image-reattach.ts
+++ b/src/renderer/src/components/native-chat/native-chat-image-reattach.ts
@@ -1,7 +1,8 @@
 import { translate } from '@/i18n/i18n'
 import type { NativeChatComposerImageAttachment } from './NativeChatComposerField'
 
-/** Why the composer can't send while it holds images Orca couldn't keep; null when it holds none. */
+/** Why the composer can't send while it holds images that couldn't be brought back; null when it
+ *  holds none. Removing always works; re-attaching only for a file, so the reason names removing. */
 export function nativeChatAttachImagesAgainReason(
   attachments: readonly NativeChatComposerImageAttachment[]
 ): string | null {
@@ -11,12 +12,12 @@ export function nativeChatAttachImagesAgainReason(
   }
   return count === 1
     ? translate(
-        'components.native-chat.composer.attachImageAgain',
-        'Attach the image again or remove it'
+        'components.native-chat.composer.removeImageToSend',
+        "An image couldn't be brought back. Remove it to send."
       )
     : translate(
-        'components.native-chat.composer.attachImagesAgain',
-        'Attach the images again or remove them'
+        'components.native-chat.composer.removeImagesToSend',
+        "Some images couldn't be brought back. Remove them to send."
       )
 }
 
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 21b37ddbb7c..f2049ba88a2 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
@@ -157,7 +157,8 @@ export function useNativeChatComposerAttachments({
           id: nextAttachmentId(),
           path,
           ...(connectionId ? { connectionId } : {})
-        }))
+        })),
+        { fromUser: true }
       )
     },
     [attachmentScopeKey, nextAttachmentId]
@@ -233,9 +234,11 @@ export function useNativeChatComposerAttachments({
   const resolvePendingImageAttachment = useCallback(
     (id: string, path: string, connectionId?: string | null) => {
       if (forgetLocalAttachment(id, true)) {
-        appendNativeChatAttachmentCache(attachmentScopeKey, [
-          { id, path, ...(connectionId ? { connectionId } : {}) }
-        ])
+        appendNativeChatAttachmentCache(
+          attachmentScopeKey,
+          [{ id, path, ...(connectionId ? { connectionId } : {}) }],
+          { fromUser: true }
+        )
       }
     },
     [attachmentScopeKey, forgetLocalAttachment]
@@ -298,12 +301,13 @@ export function readNativeChatAttachmentCache(
   return readNativeChatComposerDraft(scopeKey).images.map((image) => ({ ...image }))
 }
 
-/** Adds settled images after the ones the draft holds now; one with the name of an image to
- *  attach again takes its place. Saved at once: when Stop gives images back, the copy they came
- *  from goes right after this. */
+/** Adds settled images after the ones the draft holds now. Saved at once: when Stop gives images
+ *  back, the copy they came from goes right after this. Only an image the user attaches
+ *  (`fromUser`) takes the place of a placeholder with its file name, as a re-pick does. */
 export function appendNativeChatAttachmentCache(
   scopeKey: string,
-  appended: readonly NativeChatComposerImageAttachment[]
+  appended: readonly NativeChatComposerImageAttachment[],
+  options?: { fromUser?: boolean }
 ): void {
   if (appended.length === 0) {
     return
@@ -312,11 +316,13 @@ export function appendNativeChatAttachmentCache(
   for (const { id, path, connectionId } of appended) {
     // Preview URLs can retain the full clipboard Blob, so only the path is kept.
     const image = { id, path, ...(connectionId ? { connectionId } : {}) }
-    const marker = images.findIndex((held) => held.unavailableName === basename(path))
-    if (marker === -1) {
+    const placeholder = options?.fromUser
+      ? images.findIndex((held) => held.unavailableName === basename(path))
+      : -1
+    if (placeholder === -1) {
       images.push(image)
     } else {
-      images[marker] = image
+      images[placeholder] = image
     }
   }
   updateNativeChatComposerDraft(scopeKey, { images }, 'immediate')
diff --git a/src/renderer/src/i18n/locales/en.json b/src/renderer/src/i18n/locales/en.json
index b803ccda70d..7fa1cbcf2db 100644
--- a/src/renderer/src/i18n/locales/en.json
+++ b/src/renderer/src/i18n/locales/en.json
@@ -17765,9 +17765,12 @@
         "localAttachmentUnsupported": "Local attachments are not available for remote sessions.",
         "removeAttachment": "Remove attachment",
         "pastedImageLabel": "Pasted image",
-        "imageNotSavedWithDraft": "{{name}} wasn't saved with this draft. Attach it again to send it.",
-        "attachImageAgain": "Attach the image again or remove it",
-        "attachImagesAgain": "Attach the images again or remove them",
+        "imageNotBroughtBack": "{{name}} couldn't be brought back with this draft. Attach it again or remove it.",
+        "pastedImageNotBroughtBack": "This pasted image couldn't be brought back with this draft. Remove it, and paste it again if you still need it.",
+        "removeImageToSend": "An image couldn't be brought back. Remove it to send.",
+        "removeImagesToSend": "Some images couldn't be brought back. Remove them to send.",
+        "imageAttachAgainLabel": "Attach again",
+        "pastedImageNotKeptLabel": "Not kept",
         "imagePasteFailed": "Image paste failed.",
         "imageSaving": "Saving pasted image…",
         "worktreeNotReady": "Worktree not ready — try again in a moment.",
diff --git a/src/renderer/src/i18n/locales/es.json b/src/renderer/src/i18n/locales/es.json
index d89dff132b9..ab4630b73a4 100644
--- a/src/renderer/src/i18n/locales/es.json
+++ b/src/renderer/src/i18n/locales/es.json
@@ -15084,9 +15084,12 @@
         "localAttachmentUnsupported": "Los archivos adjuntos locales no están disponibles para sesiones remotas.",
         "removeAttachment": "Quitar archivo adjunto",
         "pastedImageLabel": "Imagen pegada",
-        "imageNotSavedWithDraft": "{{name}} no se guardó con este borrador. Adjúntala de nuevo para enviarla.",
-        "attachImageAgain": "Adjunta la imagen de nuevo o quítala",
-        "attachImagesAgain": "Adjunta las imágenes de nuevo o quítalas",
+        "imageNotBroughtBack": "No se pudo recuperar la imagen {{name}} con este borrador. Vuelve a adjuntarla o quítala.",
+        "pastedImageNotBroughtBack": "No se pudo recuperar esta imagen pegada con este borrador. Quítala y vuelve a pegarla si aún la necesitas.",
+        "removeImageToSend": "No se pudo recuperar una imagen. Quítala para enviar.",
+        "removeImagesToSend": "No se pudieron recuperar algunas imágenes. Quítalas para enviar.",
+        "imageAttachAgainLabel": "Adjuntar de nuevo",
+        "pastedImageNotKeptLabel": "No se conservó",
         "imagePasteFailed": "Error al pegar imagen.",
         "worktreeNotReady": "Worktree no está listo — intenta de nuevo en un momento.",
         "pasteUnavailable": "No se puede pegar — este chat no acepta entradas en este momento.",
diff --git a/src/renderer/src/i18n/locales/fr.json b/src/renderer/src/i18n/locales/fr.json
index f5b6686a760..f0ddc4f86d7 100644
--- a/src/renderer/src/i18n/locales/fr.json
+++ b/src/renderer/src/i18n/locales/fr.json
@@ -17568,9 +17568,12 @@
         "localAttachmentUnsupported": "Les pièces jointes locales ne sont pas disponibles pour les sessions distantes.",
         "removeAttachment": "Retirer la pièce jointe",
         "pastedImageLabel": "Image collée",
-        "imageNotSavedWithDraft": "{{name}} n'a pas été enregistrée avec ce brouillon. Joignez-la à nouveau pour l'envoyer.",
-        "attachImageAgain": "Joignez à nouveau l'image ou retirez-la",
-        "attachImagesAgain": "Joignez à nouveau les images ou retirez-les",
+        "imageNotBroughtBack": "L'image {{name}} n'a pas pu être récupérée avec ce brouillon. Joignez-la à nouveau ou retirez-la.",
+        "pastedImageNotBroughtBack": "Cette image collée n'a pas pu être récupérée avec ce brouillon. Retirez-la, puis collez-la à nouveau si vous en avez encore besoin.",
+        "removeImageToSend": "Une image n'a pas pu être récupérée. Retirez-la pour envoyer.",
+        "removeImagesToSend": "Certaines images n'ont pas pu être récupérées. Retirez-les pour envoyer.",
+        "imageAttachAgainLabel": "Joindre à nouveau",
+        "pastedImageNotKeptLabel": "Non conservée",
         "imagePasteFailed": "Échec du collage de l'image.",
         "worktreeNotReady": "Worktree pas encore prêt — réessayez dans un instant.",
         "pasteUnavailable": "Impossible de coller — ce chat n'accepte pas de saisie pour le moment.",
diff --git a/src/renderer/src/i18n/locales/ja.json b/src/renderer/src/i18n/locales/ja.json
index 2c204b78840..67443dcb9ac 100644
--- a/src/renderer/src/i18n/locales/ja.json
+++ b/src/renderer/src/i18n/locales/ja.json
@@ -17490,9 +17490,12 @@
         "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",
-        "imageNotSavedWithDraft": "{{name}} はこの下書きに保存されませんでした。送信するにはもう一度添付してください。",
-        "attachImageAgain": "画像をもう一度添付するか、削除してください",
-        "attachImagesAgain": "画像をもう一度添付するか、削除してください",
+        "imageNotBroughtBack": "{{name}} をこの下書きと一緒に復元できませんでした。もう一度添付するか、削除してください。",
+        "pastedImageNotBroughtBack": "この貼り付けた画像をこの下書きと一緒に復元できませんでした。削除して、必要であればもう一度貼り付けてください。",
+        "removeImageToSend": "復元できなかった画像があります。送信するには削除してください。",
+        "removeImagesToSend": "復元できなかった画像があります。送信するには削除してください。",
+        "imageAttachAgainLabel": "もう一度添付",
+        "pastedImageNotKeptLabel": "保持されていません",
         "imagePasteFailed": "画像の貼り付けに失敗しました。",
         "worktreeNotReady": "ワークツリーが準備できていません — しばらくしてから再試行してください。",
         "pasteUnavailable": "貼り付けできません — このチャットは現在入力を受け付けていません。",
diff --git a/src/renderer/src/i18n/locales/ko.json b/src/renderer/src/i18n/locales/ko.json
index 3a8e5a3b822..4828e4e3d4a 100644
--- a/src/renderer/src/i18n/locales/ko.json
+++ b/src/renderer/src/i18n/locales/ko.json
@@ -17490,9 +17490,12 @@
         "localAttachmentUnsupported": "원격 세션에는 로컬 첨부 파일을 사용할 수 없습니다.",
         "removeAttachment": "첨부파일 삭제",
         "pastedImageLabel": "붙여넣은 이미지",
-        "imageNotSavedWithDraft": "{{name}}은(는) 이 초안에 저장되지 않았습니다. 보내려면 다시 첨부하세요.",
-        "attachImageAgain": "이미지를 다시 첨부하거나 제거하세요",
-        "attachImagesAgain": "이미지를 다시 첨부하거나 제거하세요",
+        "imageNotBroughtBack": "{{name}}을(를) 이 초안과 함께 복원하지 못했습니다. 다시 첨부하거나 제거하세요.",
+        "pastedImageNotBroughtBack": "이 붙여넣은 이미지를 이 초안과 함께 복원하지 못했습니다. 제거한 후 필요하면 다시 붙여넣으세요.",
+        "removeImageToSend": "복원하지 못한 이미지가 있습니다. 보내려면 제거하세요.",
+        "removeImagesToSend": "복원하지 못한 이미지가 있습니다. 보내려면 제거하세요.",
+        "imageAttachAgainLabel": "다시 첨부",
+        "pastedImageNotKeptLabel": "보존되지 않음",
         "imagePasteFailed": "이미지 붙여넣기 실패.",
         "worktreeNotReady": "워크트리가 준비되지 않았습니다 — 잠시 후 다시 시도하세요.",
         "pasteUnavailable": "붙여넣을 수 없습니다 — 이 채팅은 지금 입력을 받을 수 없습니다.",
diff --git a/src/renderer/src/i18n/locales/zh.json b/src/renderer/src/i18n/locales/zh.json
index b7af46e09fd..299df53d235 100644
--- a/src/renderer/src/i18n/locales/zh.json
+++ b/src/renderer/src/i18n/locales/zh.json
@@ -17507,9 +17507,12 @@
         "localAttachmentUnsupported": "远程会话不支持本地附件。",
         "removeAttachment": "移除附件",
         "pastedImageLabel": "粘贴的图片",
-        "imageNotSavedWithDraft": "{{name}} 未随此草稿保存。请重新附加后再发送。",
-        "attachImageAgain": "请重新附加该图片或将其移除",
-        "attachImagesAgain": "请重新附加这些图片或将其移除",
+        "imageNotBroughtBack": "无法随此草稿恢复 {{name}}。请重新附加或将其移除。",
+        "pastedImageNotBroughtBack": "无法随此草稿恢复这张粘贴的图片。请将其移除，如仍需要请重新粘贴。",
+        "removeImageToSend": "有一张图片无法恢复。请将其移除后再发送。",
+        "removeImagesToSend": "有些图片无法恢复。请将其移除后再发送。",
+        "imageAttachAgainLabel": "重新附加",
+        "pastedImageNotKeptLabel": "未保留",
         "imagePasteFailed": "图片粘贴失败。",
         "worktreeNotReady": "工作树未就绪 — 请稍后重试。",
         "pasteUnavailable": "无法粘贴 — 此聊天当前不接受输入。",