fix(desktop): refuse the tray's Send like the composer and undo the exact sent turn with its files

- Run the composer's own send checks (dictation, read-only, images the model
  cannot take, a missing cloud repo or model) before the tray's Send click or
  one-key Send, with the same toast
- Find a sent suggestion's message only among turns after the one it was sent
  at, so Undo never forks from an earlier copy of the same prompt
- Read past the [attached N files] label when matching a sent prompt in the
  queue or the chat, so a send that carried files can be undone
- Put the files back on the composer when Undo takes back a sent prompt that
  is still queued
- Move the attached-files label into lib/attached-files-label.ts so the label
  and its removal stay in step

apps/examples/desktop-app/webview/app/page.tsx

@@ -2379,6 +2379,8 @@ function ChatThreadPane({
 		waiting: pendingToolApprovals.length > 0 || pendingAskQuestions.length > 0,
 		messages: displayedMessages,
 		promptsInQueue,
+		pendingAttachments,
+		onAttachFiles: handleAttachFiles,
 		onSend: handleSendSuggestion,
 		onUndoTurn: handleEditMessage,
 		onRemoveQueuedPrompt: removePromptInQueue,

apps/examples/desktop-app/webview/components/views/chat/chat-input-bar.test.tsx

@@ -3459,23 +3459,27 @@ describe("ChatInputBar suggestion tray", () => {
 		prompt = "",
 		promptVersion = 0,
 		onSend = vi.fn(),
+		attachments = [],
+		model = "test-model",
 	}: {
 		suggestions: ComposerSuggestionsController;
 		variant?: "conversation" | "welcome";
 		prompt?: string;
 		promptVersion?: number;
 		onSend?: (prompt: string) => void;
+		attachments?: Parameters<typeof ChatInputBar>[0]["attachments"];
+		model?: string;
 	}) {
 		await act(async () => {
 			root.render(
 				<WorkspaceProvider value={workspaceValue}>
 					<ChatInputBar
-						attachments={[]}
+						attachments={attachments}
 						environmentId="local"
 						executionTarget="local"
 						gitBranch="main"
 						mode="act"
-						model="test-model"
+						model={model}
 						onAbort={vi.fn()}
 						onAttachFiles={vi.fn()}
 						onEditPromptInQueue={vi.fn()}
@@ -3613,6 +3617,95 @@ describe("ChatInputBar suggestion tray", () => {
 		);
 	});
 
+	it("refuses the tray's Send, with the composer's reason, while the composer would refuse its own", async () => {
+		const suggestions = stubSuggestions();
+		const attachments = [{ id: "image", name: "photo.png", isImage: true }];
+		await renderWithSuggestions({
+			suggestions,
+			attachments,
+			model: "text-only",
+		});
+		await act(async () => {
+			subscribeToProviderModelsMock.mock.calls.at(-1)?.[0]("cline", [
+				{ id: "text-only", name: "Text only", inputModalities: ["text"] },
+			]);
+		});
+
+		await act(async () => {
+			container
+				.querySelector<HTMLButtonElement>(
+					'[data-testid="suggestion-legend"] button[data-verb="send"]',
+				)
+				?.click();
+		});
+		await act(async () => {
+			container.querySelector("textarea")?.dispatchEvent(
+				new KeyboardEvent("keydown", {
+					bubbles: true,
+					cancelable: true,
+					code: "Digit1",
+					key: "!",
+					ctrlKey: true,
+					shiftKey: true,
+				}),
+			);
+		});
+
+		expect(suggestions.send).not.toHaveBeenCalled();
+		expect(toastMock).toHaveBeenCalledTimes(2);
+		expect(toastMock).toHaveBeenCalledWith(
+			expect.objectContaining({
+				title: "This model doesn’t support image input",
+			}),
+		);
+		expect(container.textContent).toContain("photo.png");
+
+		await renderWithSuggestions({
+			suggestions,
+			attachments: [],
+			model: "text-only",
+		});
+		await act(async () => {
+			container
+				.querySelector<HTMLButtonElement>(
+					'[data-testid="suggestion-legend"] button[data-verb="send"]',
+				)
+				?.click();
+		});
+
+		expect(suggestions.send).toHaveBeenCalledTimes(1);
+	});
+
+	it("refuses the tray's Send while dictation is filling the box", async () => {
+		loadProviderModelCatalogMock.mockResolvedValue(
+			providerCatalog({
+				providerId: "vercel-ai-gateway",
+				providerName: "Vercel AI Gateway",
+				modelId: "openai/gpt-realtime-whisper",
+				modelName: "GPT-4o mini Transcribe",
+				supportsStreaming: true,
+			}),
+		);
+		const suggestions = stubSuggestions();
+		await renderWithSuggestions({ suggestions });
+		await vi.waitFor(() => {
+			expect(speechInputMockState.current).not.toBeNull();
+		});
+		await act(async () => {
+			speechInputMockState.current?.onActiveChange?.(true);
+		});
+
+		await act(async () => {
+			container
+				.querySelector<HTMLButtonElement>(
+					'[data-testid="suggestion-legend"] button[data-verb="send"]',
+				)
+				?.click();
+		});
+
+		expect(suggestions.send).not.toHaveBeenCalled();
+	});
+
 	describe("one-key Send", () => {
 		let drafts: Map<string, string>;
 		beforeEach(() => {

apps/examples/desktop-app/webview/components/views/chat/chat-input-bar.tsx

@@ -567,13 +567,23 @@ function ChatInputBarImpl({
 			steeringPromptRef.current = false;
 		}
 	};
-	const handleSend = useCallback(() => {
-		if (speechInputActive || readOnly) return;
+	const composerRefusesSend = useCallback(() => {
+		if (speechInputActive || readOnly) return true;
 		if (unsupportedDraftImageCount > 0) {
 			reportUnsupportedImages();
-			return;
+			return true;
 		}
-		if (needsCloudRepository || needsCloudModel) return;
+		return needsCloudRepository || needsCloudModel;
+	}, [
+		needsCloudRepository,
+		needsCloudModel,
+		readOnly,
+		speechInputActive,
+		unsupportedDraftImageCount,
+		reportUnsupportedImages,
+	]);
+	const handleSend = useCallback(() => {
+		if (composerRefusesSend()) return;
 		const prompt = promptInput.trim();
 		if (!prompt) {
 			toast({
@@ -586,18 +596,7 @@ function ChatInputBarImpl({
 		suggestions?.submitted(prompt);
 		setPromptInput("");
 		onSend(prompt);
-	}, [
-		needsCloudRepository,
-		needsCloudModel,
-		readOnly,
-		onSend,
-		promptInput,
-		setPromptInput,
-		speechInputActive,
-		suggestions,
-		unsupportedDraftImageCount,
-		reportUnsupportedImages,
-	]);
+	}, [composerRefusesSend, onSend, promptInput, setPromptInput, suggestions]);
 	const fileInputRef = useRef<HTMLInputElement | null>(null);
 	const [transcriptionTarget, setTranscriptionTarget] =
 		useState<TranscriptionModelTarget | null>(null);
@@ -1708,6 +1707,7 @@ function ChatInputBarImpl({
 					composerInputRef={promptInputRef}
 					composerMenuOpen={slashOpen || mentionOpen}
 					draft={promptInput}
+					refusesSend={composerRefusesSend}
 					setDraft={setPromptInput}
 					suggestions={suggestions}
 				/>

apps/examples/desktop-app/webview/components/views/chat/suggestion-tray/suggestion-tray.tsx

@@ -43,6 +43,7 @@ export type SuggestionTrayProps = {
 	suggestions: ComposerSuggestionsController;
 	draft: string;
 	setDraft: (value: string) => void;
+	refusesSend: () => boolean;
 	composerInputRef: RefObject<HTMLTextAreaElement | null>;
 	/** The slash or @ menu is open over the message box; the tray steps aside. */
 	composerMenuOpen: boolean;
@@ -156,6 +157,7 @@ export function SuggestionTray({
 	suggestions,
 	draft,
 	setDraft,
+	refusesSend,
 	composerInputRef,
 	composerMenuOpen,
 }: SuggestionTrayProps) {
@@ -176,6 +178,8 @@ export function SuggestionTray({
 	draftRef.current = draft;
 	const setDraftRef = useRef(setDraft);
 	setDraftRef.current = setDraft;
+	const refusesSendRef = useRef(refusesSend);
+	refusesSendRef.current = refusesSend;
 	const factsRef = useRef({ width, menuOpen: composerMenuOpen, dialogOpen });
 	factsRef.current = { width, menuOpen: composerMenuOpen, dialogOpen };
 	const movedByKeyRef = useRef(false);
@@ -196,6 +200,7 @@ export function SuggestionTray({
 					input.setSelectionRange(end, end);
 				}, 0);
 			},
+			refusesSend: () => refusesSendRef.current(),
 		}),
 		[composerInputRef],
 	);

apps/examples/desktop-app/webview/hooks/composer-suggestions/sent-prompt.test.ts

@@ -0,0 +1,76 @@
+import { describe, expect, it } from "vitest";
+import {
+	withAttachedFilesLabel,
+	withoutAttachedFilesLabel,
+} from "@/lib/attached-files-label";
+import { findSentMessage, samePrompt, snapshotAtSend } from "./sent-prompt";
+import { userMessage } from "./test-support/fixtures";
+
+const PROMPT = "Run the tests and fix what fails";
+
+const earlierTurns = [
+	userMessage("m-earlier", PROMPT, 1),
+	userMessage("m-between", "Refactor the parser", 2),
+];
+const sentAfter = (messages: typeof earlierTurns) =>
+	snapshotAtSend({ messages, pendingAttachments: [] }).runCount;
+
+describe("findSentMessage", () => {
+	it("finds the prompt's own message after the run count it was sent at, never an earlier copy", () => {
+		const messages = [
+			...earlierTurns,
+			userMessage("m-sent", withAttachedFilesLabel(PROMPT, 1), 3),
+		];
+
+		expect(findSentMessage(messages, PROMPT, sentAfter(earlierTurns))).toEqual({
+			messageId: "m-sent",
+			runCount: 3,
+		});
+	});
+
+	it("finds nothing while only an earlier copy exists", () => {
+		expect(
+			findSentMessage(earlierTurns, PROMPT, sentAfter(earlierTurns)),
+		).toBeUndefined();
+	});
+});
+
+describe("snapshotAtSend", () => {
+	it("takes the newest user turn's run count, or 0 for an empty chat, and the files going with the send", () => {
+		const notes = new File(["hello"], "notes.txt");
+		expect(snapshotAtSend({ messages: [], pendingAttachments: [] })).toEqual({
+			runCount: 0,
+			attachments: [],
+		});
+		expect(
+			snapshotAtSend({ messages: earlierTurns, pendingAttachments: [notes] }),
+		).toEqual({ runCount: 2, attachments: [notes] });
+	});
+});
+
+describe("samePrompt", () => {
+	it("reads past the attached-files label the desktop adds to a sent prompt", () => {
+		expect(samePrompt(withAttachedFilesLabel(PROMPT, 1), PROMPT)).toBe(true);
+		expect(samePrompt(withAttachedFilesLabel(PROMPT, 2), PROMPT)).toBe(true);
+		expect(samePrompt(withAttachedFilesLabel("", 2), "")).toBe(true);
+		expect(samePrompt(withAttachedFilesLabel(PROMPT, 1), "Run the tests")).toBe(
+			false,
+		);
+	});
+});
+
+describe("attached-files label", () => {
+	it("comes off exactly as it went on", () => {
+		for (const prompt of ["", PROMPT, "First line\n\nSecond line"]) {
+			for (const fileCount of [0, 1, 2]) {
+				expect(
+					withoutAttachedFilesLabel(withAttachedFilesLabel(prompt, fileCount)),
+				).toBe(prompt);
+			}
+		}
+		expect(withAttachedFilesLabel(PROMPT, 2)).toBe(
+			`${PROMPT}\n\n[attached 2 files]`,
+		);
+		expect(withAttachedFilesLabel("", 1)).toBe("[attached 1 file]");
+	});
+});

apps/examples/desktop-app/webview/hooks/composer-suggestions/sent-prompt.ts

@@ -1,6 +1,8 @@
 import { formatDisplayUserInput } from "@cline/shared/browser";
 import { buildUserRunCountMap } from "@/components/views/chat/messages/group-messages";
+import { withoutAttachedFilesLabel } from "@/lib/attached-files-label";
 import type { ChatMessage } from "@/lib/chat-schema";
+import type { ComposerSuggestionsOptions } from "./types";
 
 /** A prompt taken back from the queue goes in front of anything typed since, never over it. */
 export function takenBackDraft(prompt: string, draft: string): string {
@@ -10,21 +12,42 @@ export function takenBackDraft(prompt: string, draft: string): string {
 }
 
 export function samePrompt(text: string, prompt: string): boolean {
-	return formatDisplayUserInput(text.trim()).trim() === prompt.trim();
+	return (
+		formatDisplayUserInput(withoutAttachedFilesLabel(text.trim())).trim() ===
+		prompt.trim()
+	);
 }
 
-/** The last user message showing `prompt`, with the run count a fork from before it needs. */
+/** Taken when a suggestion is sent: its message will follow `runCount`, and `attachments` went with it. */
+export type SendSnapshot = { runCount: number; attachments: readonly File[] };
+
+export function snapshotAtSend({
+	messages,
+	pendingAttachments,
+}: Pick<
+	ComposerSuggestionsOptions,
+	"messages" | "pendingAttachments"
+>): SendSnapshot {
+	return {
+		runCount: Math.max(0, ...buildUserRunCountMap(messages).values()),
+		attachments: pendingAttachments,
+	};
+}
+
+/**
+ * The message a prompt sent at `afterRunCount` became, with the run count a
+ * fork from before it needs. Only later turns count, so a copy sent earlier
+ * is never taken for it.
+ */
 export function findSentMessage(
 	messages: ChatMessage[],
 	prompt: string,
+	afterRunCount: number,
 ): { messageId: string; runCount: number } | undefined {
-	const runCounts = buildUserRunCountMap(messages);
-	const message = messages.findLast(
-		(candidate) =>
-			candidate.role === "user" && samePrompt(candidate.content, prompt),
-	);
-	const runCount = message ? runCounts.get(message) : undefined;
-	return message && runCount !== undefined
-		? { messageId: message.id, runCount }
-		: undefined;
+	for (const [message, runCount] of buildUserRunCountMap(messages)) {
+		if (runCount > afterRunCount && samePrompt(message.content, prompt)) {
+			return { messageId: message.id, runCount };
+		}
+	}
+	return undefined;
 }

apps/examples/desktop-app/webview/hooks/composer-suggestions/test-support/harness.tsx

@@ -39,6 +39,8 @@ export function defaultOptions(
 		waiting: false,
 		messages: [],
 		promptsInQueue: [],
+		pendingAttachments: [],
+		onAttachFiles: vi.fn(),
 		onSend: vi.fn(),
 		onUndoTurn: vi.fn(async () => undefined),
 		onRemoveQueuedPrompt: vi.fn(async (promptId: string) =>
@@ -69,6 +71,7 @@ function Harness({
 					composerInputRef={composerInputRef}
 					composerMenuOpen={false}
 					draft={draft}
+					refusesSend={() => false}
 					setDraft={setDraft}
 					suggestions={suggestions}
 				/>

apps/examples/desktop-app/webview/hooks/composer-suggestions/types.ts

@@ -21,6 +21,7 @@ export type SuggestionComposer = {
 	draft(): string;
 	setDraft(value: string): void;
 	focus(): void;
+	refusesSend(): boolean;
 };
 
 /** What the tray's view depends on that only the composer knows. */
@@ -45,6 +46,10 @@ export type ComposerSuggestionsOptions = {
 	waiting: boolean;
 	messages: ChatMessage[];
 	promptsInQueue: readonly PromptInQueue[];
+	/** The files the composer's next send carries. */
+	pendingAttachments: readonly File[];
+	/** Puts files back on the composer, as a send that never left does. */
+	onAttachFiles: (files: File[]) => void;
 	/** Submits a one-key Send's prompt. It never came from the box, which may hold text typed during the verdict wait, so the box stays as it is. */
 	onSend: (prompt: string) => void;
 	/** Forks the session from before `runCount` with `content` as the new draft. */

apps/examples/desktop-app/webview/hooks/composer-suggestions/use-tray-keys.test.ts

@@ -197,6 +197,7 @@ describe("useSuggestionTrayKeys", () => {
 		expect(event.defaultPrevented).toBe(true);
 		expect(tray.options().onRemoveQueuedPrompt).toHaveBeenCalledWith("q1");
 		expect(tray.composer().value).toBe(SENT_PROMPT);
+		expect(tray.options().onAttachFiles).not.toHaveBeenCalled();
 		expect(actions("undo")).toEqual([]);
 		expect(tray.options().onUndoTurn).not.toHaveBeenCalled();
 	});
@@ -273,6 +274,85 @@ describe("useSuggestionTrayKeys", () => {
 		);
 	});
 
+	it("Ctrl+3 forks from a sent prompt that went with a file, never an earlier copy", async () => {
+		const onUndoTurn = vi.fn(async () => undefined);
+		const abort = vi.fn(async () => undefined);
+		const earlierTurns = [
+			userMessage("m-earlier", SENT_PROMPT, 1),
+			userMessage("m-between", "Now add a changelog entry", 2),
+		];
+		const tray = await mountReady({
+			abort,
+			onUndoTurn,
+			messages: earlierTurns,
+		});
+		await sendFirstSuggestion(tray);
+		await tray.update({
+			status: "running",
+			messages: [
+				...earlierTurns,
+				userMessage("m-sent", `${SENT_PROMPT}\n\n[attached 1 file]`, 3),
+			],
+		});
+
+		await press(tray.composer(), UNDO);
+		await tray.update({ status: "cancelled" });
+		await settle(100);
+
+		expect(abort).toHaveBeenCalledTimes(1);
+		expect(onUndoTurn).toHaveBeenCalledTimes(1);
+		expect(onUndoTurn).toHaveBeenCalledWith("m-sent", SENT_PROMPT, 3);
+	});
+
+	it("Ctrl+3 is inert while only an earlier copy of the sent prompt exists", async () => {
+		const onUndoTurn = vi.fn(async () => undefined);
+		const abort = vi.fn(async () => undefined);
+		const tray = await mountReady({
+			abort,
+			onUndoTurn,
+			messages: [
+				userMessage("m-earlier", SENT_PROMPT, 1),
+				userMessage("m-between", "Now add a changelog entry", 2),
+			],
+		});
+		await sendFirstSuggestion(tray);
+		await tray.update({ status: "running" });
+
+		const event = await press(tray.composer(), UNDO);
+
+		expect(event.defaultPrevented).toBe(false);
+		expect(
+			tray.container.querySelector('[data-testid="suggestion-undo"]'),
+		).toBeNull();
+		expect(abort).not.toHaveBeenCalled();
+		expect(actions("undo")).toEqual([]);
+		expect(onUndoTurn).not.toHaveBeenCalled();
+	});
+
+	it("Ctrl+3 takes back a queued sent prompt that went with a file, and puts the file back", async () => {
+		const notes = new File(["hello"], "notes.txt");
+		const tray = await mountReady({ pendingAttachments: [notes] });
+		await sendFirstSuggestion(tray);
+		await tray.update({
+			pendingAttachments: [],
+			promptsInQueue: [
+				{
+					id: "q1",
+					prompt: `${SENT_PROMPT}\n\n[attached 1 file]`,
+					steer: false,
+				},
+			],
+		});
+
+		await press(tray.composer(), UNDO);
+
+		expect(tray.options().onRemoveQueuedPrompt).toHaveBeenCalledWith("q1");
+		expect(tray.composer().value).toBe(SENT_PROMPT);
+		expect(tray.options().onAttachFiles).toHaveBeenCalledExactlyOnceWith([
+			notes,
+		]);
+	});
+
 	it("takes a queued sent prompt back once when Undo is pressed again while the removal is in flight", async () => {
 		const queued = { id: "q1", prompt: SENT_PROMPT, steer: false };
 		const removal = deferred<typeof queued | undefined>();

apps/examples/desktop-app/webview/hooks/composer-suggestions/use-tray-keys.ts

@@ -77,6 +77,7 @@ export function runSuggestionVerb(
 			controller.use(view.highlighted, input, composer);
 			return true;
 		case "send":
+			if (view.canSend && composer.refusesSend()) return true;
 			void controller.send(view, input);
 			return true;
 		case "skip":

apps/examples/desktop-app/webview/hooks/composer-suggestions/use-undo-sent.ts

@@ -8,7 +8,12 @@ import { type RefObject, useCallback, useRef } from "react";
 import { BUSY_STATUSES } from "@/hooks/use-chat-session";
 import { toast } from "@/hooks/use-toast";
 import type { ChatSessionStatus } from "@/lib/chat-schema";
-import { findSentMessage, samePrompt, takenBackDraft } from "./sent-prompt";
+import {
+	findSentMessage,
+	type SendSnapshot,
+	samePrompt,
+	takenBackDraft,
+} from "./sent-prompt";
 import { delay } from "./timing";
 import type {
 	ComposerSuggestionsOptions,
@@ -31,6 +36,7 @@ export function useUndoSent({
 	localRef,
 	latest,
 	dispatch,
+	sendSnapshotRef,
 }: {
 	status: ChatSessionStatus;
 	onUndoTurn: ComposerSuggestionsOptions["onUndoTurn"];
@@ -38,6 +44,7 @@ export function useUndoSent({
 	localRef: RefObject<SuggestionsLocal>;
 	latest: RefObject<ComposerSuggestionsOptions>;
 	dispatch: SuggestionsDispatch;
+	sendSnapshotRef: RefObject<SendSnapshot>;
 }) {
 	const statusRef = useRef(status);
 	statusRef.current = status;
@@ -47,38 +54,39 @@ export function useUndoSent({
 	const undoInFlightRef = useRef(false);
 
 	/**
-	 * A sent prompt the queue still holds comes back into the box with no verb,
-	 * since no turn ran. Otherwise, including when the runtime started it before
-	 * the removal landed, the turn is forked away from before the sent message,
-	 * after stopping a run the fork would refuse.
+	 * A sent prompt the queue still holds comes back into the box with the files
+	 * that went with it and no verb, since no turn ran. Otherwise, including when
+	 * the runtime started it before the removal landed, the turn is forked away
+	 * from before the sent message, after stopping a run the fork would refuse.
 	 */
 	const undoSent = useCallback(
 		async (composer: SuggestionComposer) => {
 			const sent = localRef.current.sent;
 			if (!sent || undoInFlightRef.current) return;
 			undoInFlightRef.current = true;
-			const { abort, onRemoveQueuedPrompt, promptsInQueue } = latest.current;
+			const { abort, onAttachFiles, onRemoveQueuedPrompt, promptsInQueue } =
+				latest.current;
 			try {
 				const queuedPrompt = promptsInQueue.find((item) =>
 					samePrompt(item.prompt, sent.prompt),
 				);
-				/** A prompt still queued has no message of its own, so a match now is an earlier copy. */
-				let earlierCopyId: string | undefined;
 				if (queuedPrompt) {
-					earlierCopyId = findSentMessage(
-						latest.current.messages,
-						sent.prompt,
-					)?.messageId;
 					if (await onRemoveQueuedPrompt(queuedPrompt.id)) {
 						composer.setDraft(takenBackDraft(sent.prompt, composer.draft()));
+						const { attachments } = sendSnapshotRef.current;
+						if (attachments.length > 0) onAttachFiles([...attachments]);
 						composer.focus();
 						dispatch({ type: "unsent" });
 						return;
 					}
 					if (localRef.current.sent !== sent) return;
 				}
-				const target = findSentMessage(latest.current.messages, sent.prompt);
-				if (!target || target.messageId === earlierCopyId) {
+				const target = findSentMessage(
+					latest.current.messages,
+					sent.prompt,
+					sendSnapshotRef.current.runCount,
+				);
+				if (!target) {
 					if (queuedPrompt) toast({ title: NOT_TAKEN_BACK });
 					return;
 				}
@@ -119,7 +127,7 @@ export function useUndoSent({
 				undoInFlightRef.current = false;
 			}
 		},
-		[dispatch, invoke, latest, localRef],
+		[dispatch, invoke, latest, localRef, sendSnapshotRef],
 	);
 
 	return undoSent;

apps/examples/desktop-app/webview/hooks/composer-suggestions/use-verbs.ts

@@ -14,6 +14,7 @@ import {
 	useCallback,
 	useRef,
 } from "react";
+import { type SendSnapshot, snapshotAtSend } from "./sent-prompt";
 import { delay, msSinceExposed } from "./timing";
 import type {
 	ComposerSuggestionsOptions,
@@ -33,6 +34,7 @@ export function useSuggestionVerbs({
 	lastSkip,
 	setLastSkip,
 	setSendingItemId,
+	sendSnapshotRef,
 }: {
 	invoke: SuggestionsInvoke;
 	boundRef: RefObject<string>;
@@ -42,6 +44,7 @@ export function useSuggestionVerbs({
 	lastSkip: LastSkip | undefined;
 	setLastSkip: Dispatch<SetStateAction<LastSkip | undefined>>;
 	setSendingItemId: Dispatch<SetStateAction<string | undefined>>;
+	sendSnapshotRef: RefObject<SendSnapshot>;
 }) {
 	/** A one-key Send is waiting for its verdict; another press then sends nothing. */
 	const sendInFlightRef = useRef(false);
@@ -128,6 +131,7 @@ export function useSuggestionVerbs({
 				]);
 				if (verdict?.outcome === "refused") return;
 				if (boundRef.current !== boundSessionId) return;
+				sendSnapshotRef.current = snapshotAtSend(latest.current);
 				latest.current.onSend(ref.prompt);
 				dispatch({ type: "sent", ref });
 			} finally {
@@ -141,6 +145,7 @@ export function useSuggestionVerbs({
 			invoke,
 			latest,
 			localRef,
+			sendSnapshotRef,
 			setSendingItemId,
 			signalInert,
 		],
@@ -259,9 +264,10 @@ export function useSuggestionVerbs({
 				itemId: used.itemId,
 				input: "key",
 			});
+			sendSnapshotRef.current = snapshotAtSend(latest.current);
 			dispatch({ type: "sent" });
 		},
-		[dispatch, invoke, localRef],
+		[dispatch, invoke, latest, localRef, sendSnapshotRef],
 	);
 
 	const move = useCallback(

apps/examples/desktop-app/webview/hooks/use-chat-session.ts

@@ -49,6 +49,7 @@ import type {
 	ToolCallUpdateEvent,
 } from "@/hooks/chat-session/types";
 import { toast } from "@/hooks/use-toast";
+import { withAttachedFilesLabel } from "@/lib/attached-files-label";
 import {
 	type ChatMessage,
 	ChatMessageImageSchema,
@@ -1898,10 +1899,7 @@ export function useChatSession(environmentId: string) {
 					0,
 					attachmentCount - userImages.length,
 				);
-				const userLabel =
-					attachedFileCount > 0
-						? `${prompt}${prompt.length > 0 ? "\n\n" : ""}[attached ${attachedFileCount} file${attachedFileCount === 1 ? "" : "s"}]`
-						: prompt;
+				const userLabel = withAttachedFilesLabel(prompt, attachedFileCount);
 				const promptId = parsed.promptId?.trim();
 				activeAssistantMessageIdRef.current = null;
 				setActiveAssistantMessageId(null);
@@ -2837,10 +2835,7 @@ export function useChatSession(environmentId: string) {
 			const attachedFileCount = attachedFiles.filter(
 				(file) => !imageAttachmentMediaType(file),
 			).length;
-			const userLabel =
-				attachedFileCount > 0
-					? `${trimmed}${trimmed.length > 0 ? "\n\n" : ""}[attached ${attachedFileCount} file${attachedFileCount === 1 ? "" : "s"}]`
-					: trimmed;
+			const userLabel = withAttachedFilesLabel(trimmed, attachedFileCount);
 			const shouldQueue =
 				Boolean(activeSessionId) &&
 				(hasEarlierPromptSubmission ||

apps/examples/desktop-app/webview/hooks/use-composer-suggestions.ts

@@ -20,6 +20,7 @@ import {
 import { exposedSuggestionMemory } from "@/hooks/composer-suggestions/exposed-memory";
 import {
 	findSentMessage,
+	type SendSnapshot,
 	samePrompt,
 } from "@/hooks/composer-suggestions/sent-prompt";
 import type {
@@ -57,6 +58,10 @@ export function useComposerSuggestions(
 	localRef.current = local;
 	const latest = useRef(options);
 	latest.current = options;
+	const sendSnapshotRef = useRef<SendSnapshot>({
+		runCount: 0,
+		attachments: [],
+	});
 
 	const { invoke, boundRef } = useSlotBinding({
 		enabled,
@@ -100,7 +105,8 @@ export function useComposerSuggestions(
 		return () => clearTimeout(timer);
 	}, [local.pendingSince, local.readyAt, local.staleUntil, now]);
 
-	const sentPrompt = local.sent?.prompt;
+	const sent = local.sent;
+	const sentPrompt = sent?.prompt;
 	const queuedSent = useMemo(
 		() =>
 			sentPrompt === undefined
@@ -112,10 +118,14 @@ export function useComposerSuggestions(
 	);
 	const sentMessage = useMemo(
 		() =>
-			sentPrompt === undefined
+			sent === undefined
 				? undefined
-				: findSentMessage(options.messages, sentPrompt),
-		[options.messages, sentPrompt],
+				: findSentMessage(
+						options.messages,
+						sent.prompt,
+						sendSnapshotRef.current.runCount,
+					),
+		[options.messages, sent],
 	);
 	const canUndo = Boolean(queuedSent || sentMessage);
 	const queued = options.promptsInQueue.length;
@@ -179,6 +189,7 @@ export function useComposerSuggestions(
 		lastSkip,
 		setLastSkip,
 		setSendingItemId,
+		sendSnapshotRef,
 	});
 	const undoSent = useUndoSent({
 		status,
@@ -187,6 +198,7 @@ export function useComposerSuggestions(
 		localRef,
 		latest,
 		dispatch,
+		sendSnapshotRef,
 	});
 
 	return useMemo<ComposerSuggestionsController>(

apps/examples/desktop-app/webview/lib/attached-files-label.ts

@@ -0,0 +1,15 @@
+const ATTACHED_FILES_LABEL = /(?:^|\n\n)\[attached \d+ files?\]$/;
+
+/** How a sent prompt shows the non-image files that went with it. */
+export function withAttachedFilesLabel(
+	prompt: string,
+	fileCount: number,
+): string {
+	if (fileCount <= 0) return prompt;
+	const label = `[attached ${fileCount} file${fileCount === 1 ? "" : "s"}]`;
+	return prompt ? `${prompt}\n\n${label}` : label;
+}
+
+export function withoutAttachedFilesLabel(content: string): string {
+	return content.replace(ATTACHED_FILES_LABEL, "");
+}