test(ai-toolbar): cover normalized clipboard paste paths

src/components/ai-toolbar.tsx

@@ -52,15 +52,18 @@ async function getClipboardBlobIdentity(blob: Blob): Promise<string> {
 	return (hash >>> 0).toString(16).padStart(8, "0");
 }
 
-async function createClipboardFallbackFile(blob: Blob): Promise<File> {
+async function normalizeClipboardImageFile(blob: Blob): Promise<File> {
 	const identity = await getClipboardBlobIdentity(blob);
-	const extension = blob.type.split("/")[1] || "png";
+	return new File([blob], `clipboard-image-${identity}`, {
-	return new File([blob], `clipboard-image-${identity}.${extension}`, {
 		type: blob.type,
 		lastModified: 0,
 	});
 }
 
+async function normalizeClipboardImageFiles(files: File[]): Promise<File[]> {
+	return Promise.all(files.map((file) => normalizeClipboardImageFile(file)));
+}
+
 // ─── Shared shortcuts list (rendered in both HoverCard and Popover) ───────────
 
 function ShortcutsList({ os }: { os: Os }) {
@@ -194,7 +197,9 @@ export const AIToolbar = ({
 			const images = extractAllImagesFromClipboard(e.clipboardData ?? null);
 			if (images.length > 0) {
 				e.preventDefault();
-				onImagesSelectRef.current(images);
+				void normalizeClipboardImageFiles(images).then((normalizedImages) => {
+					onImagesSelectRef.current(normalizedImages);
+				});
 			}
 		};
 
@@ -241,7 +246,7 @@ export const AIToolbar = ({
 					for (const mimeType of typesToTry) {
 						try {
 							const blob = await clipboardItem.getType(mimeType);
-							files.push(await createClipboardFallbackFile(blob));
+							files.push(await normalizeClipboardImageFile(blob));
 							break; // got this item, move to next clipboardItem
 						} catch {
 							// NotFoundError — type not present, try next
@@ -359,7 +364,11 @@ export const AIToolbar = ({
 									);
 									if (images.length > 0) {
 										e.preventDefault();
-										onImagesSelect(images);
+										void normalizeClipboardImageFiles(images).then(
+											(normalizedImages) => {
+												onImagesSelect(normalizedImages);
+											},
+										);
 									}
 								}}
 							/>

tests/ai-toolbar.test.ts

@@ -405,14 +405,17 @@ describe("AI toolbar paste capture", () => {
 		const { textareaProps } = await renderToolbarBoundary({ onImagesSelect });
 		const preventDefault = mock();
 
-		textareaProps.onPaste?.({
+		await textareaProps.onPaste?.({
 			clipboardData: createClipboardData([image]),
 			preventDefault,
 		} as unknown as React.ClipboardEvent<HTMLTextAreaElement>);
+		await new Promise((resolve) => setTimeout(resolve, 0));
 
 		expect(preventDefault).toHaveBeenCalledTimes(1);
 		expect(onImagesSelect).toHaveBeenCalledTimes(1);
-		expect(onImagesSelect).toHaveBeenCalledWith([image]);
+		expect(onImagesSelect.mock.calls[0]?.[0][0]?.name).toMatch(
+			/^clipboard-image-/,
+		);
 	});
 
 	test("textarea-targeted paste bypasses the document listeners so the focused textarea owns the paste", async () => {
@@ -446,12 +449,15 @@ describe("AI toolbar paste capture", () => {
 		expect(preventDefault).not.toHaveBeenCalled();
 		expect(onImagesSelect).not.toHaveBeenCalled();
 
-		textareaProps.onPaste?.(
+		await textareaProps.onPaste?.(
 			pasteEvent as unknown as React.ClipboardEvent<HTMLTextAreaElement>,
 		);
+		await new Promise((resolve) => setTimeout(resolve, 0));
 		expect(preventDefault).toHaveBeenCalledTimes(1);
 		expect(onImagesSelect).toHaveBeenCalledTimes(1);
-		expect(onImagesSelect).toHaveBeenCalledWith([image]);
+		expect(onImagesSelect.mock.calls[0]?.[0][0]?.name).toMatch(
+			/^clipboard-image-/,
+		);
 
 		handleDocumentPaste(pasteEvent as unknown as Event);
 		expect(preventDefault).toHaveBeenCalledTimes(1);
@@ -524,6 +530,24 @@ describe("AI toolbar paste capture", () => {
 		expect(onAiCreate).not.toHaveBeenCalled();
 	});
 
+	test("Mod+Enter ignores Alt-modified submissions", async () => {
+		const onAiCreate = mock();
+
+		const { textareaProps } = await renderToolbarBoundary({
+			aiPrompt: "Draft a kickoff",
+			onAiCreate,
+		});
+		const event = createTextareaKeydownEvent({
+			ctrlKey: true,
+			altKey: true,
+		});
+
+		textareaProps.onKeyDown?.(event);
+
+		expect(event.preventDefault).not.toHaveBeenCalled();
+		expect(onAiCreate).not.toHaveBeenCalled();
+	});
+
 	test("Mod+Enter does not trigger AI generation while loading", async () => {
 		const onAiCreate = mock();
 
@@ -627,10 +651,13 @@ describe("AI toolbar paste capture", () => {
 			clipboardData: createClipboardData([image]),
 			preventDefault,
 		} as unknown as Event);
+		await new Promise((resolve) => setTimeout(resolve, 0));
 
 		expect(preventDefault).toHaveBeenCalledTimes(1);
 		expect(onImagesSelect).toHaveBeenCalledTimes(1);
-		expect(onImagesSelect).toHaveBeenCalledWith([image]);
+		expect(onImagesSelect.mock.calls[0]?.[0][0]?.name).toMatch(
+			/^clipboard-image-/,
+		);
 	});
 
 	test("Ctrl/Cmd+V fallback forwards clipboard images for non-editable targets", async () => {
@@ -731,6 +758,45 @@ describe("AI toolbar paste capture", () => {
 		);
 	});
 
+	test("clipboard fallback keeps the same synthesized identity across MIME aliases for identical content", async () => {
+		const onImagesSelect = mock();
+		const reads = [
+			async () => [
+				{
+					types: ["image/png"],
+					getType: async () => new Blob(["same-image"], { type: "image/png" }),
+				},
+			],
+			async () => [
+				{
+					types: ["image/x-png"],
+					getType: async () => new Blob(["same-image"], { type: "image/x-png" }),
+				},
+			],
+		];
+		const clipboardRead = mock(async () => (await reads.shift()?.()) ?? []);
+
+		(globalThis as { navigator?: Navigator }).navigator = {
+			clipboard: { read: clipboardRead },
+		} as Navigator;
+
+		await renderToolbar({ onImagesSelect });
+
+		const handleDocumentKeydown = getDocumentListener("keydown");
+
+		await handleDocumentKeydown(
+			createDocumentKeydownEvent({ ctrlKey: true }),
+		);
+		await handleDocumentKeydown(
+			createDocumentKeydownEvent({ ctrlKey: true }),
+		);
+
+		expect(onImagesSelect).toHaveBeenCalledTimes(2);
+		expect(onImagesSelect.mock.calls[0]?.[0][0]?.name).toBe(
+			onImagesSelect.mock.calls[1]?.[0][0]?.name,
+		);
+	});
+
 	test("async clipboard fallback does not double-handle a paste already handled by the synchronous document paste flow", async () => {
 		const onImagesSelect = mock();
 		const clipboardRead = mock(async () => [
@@ -778,7 +844,9 @@ describe("AI toolbar paste capture", () => {
 		expect(preventDefault).toHaveBeenCalledTimes(1);
 		expect(clipboardRead).not.toHaveBeenCalled();
 		expect(onImagesSelect).toHaveBeenCalledTimes(1);
-		expect(onImagesSelect).toHaveBeenCalledWith([image]);
+		expect(onImagesSelect.mock.calls[0]?.[0][0]?.name).toMatch(
+			/^clipboard-image-/,
+		);
 	});
 
 	test("global paste listeners only arm when AI paste capture is usable, and disarm on cleanup", async () => {