diff --git a/src/components/ai-toolbar.tsx b/src/components/ai-toolbar.tsx
index e7622f9..9ec0f06 100644
--- a/src/components/ai-toolbar.tsx
+++ b/src/components/ai-toolbar.tsx
@@ -40,12 +40,24 @@ function useOs(): Os {
 	return os;
 }
 
-function createClipboardFallbackFile(blob: Blob, index: number): File {
-	const createdAt = Date.now() + index;
+async function getClipboardBlobIdentity(blob: Blob): Promise<string> {
+	const bytes = new Uint8Array(await blob.arrayBuffer());
+	let hash = 2166136261;
+
+	for (const byte of bytes) {
+		hash ^= byte;
+		hash = Math.imul(hash, 16777619);
+	}
+
+	return (hash >>> 0).toString(16).padStart(8, "0");
+}
+
+async function createClipboardFallbackFile(blob: Blob): Promise<File> {
+	const identity = await getClipboardBlobIdentity(blob);
 	const extension = blob.type.split("/")[1] || "png";
-	return new File([blob], `clipboard-image-${createdAt}.${extension}`, {
+	return new File([blob], `clipboard-image-${identity}.${extension}`, {
 		type: blob.type,
-		lastModified: createdAt,
+		lastModified: 0,
 	});
 }
 
@@ -229,7 +241,7 @@ export const AIToolbar = ({
 					for (const mimeType of typesToTry) {
 						try {
 							const blob = await clipboardItem.getType(mimeType);
-							files.push(createClipboardFallbackFile(blob, files.length));
+							files.push(await createClipboardFallbackFile(blob));
 							break; // got this item, move to next clipboardItem
 						} catch {
 							// NotFoundError — type not present, try next
@@ -317,6 +329,7 @@ export const AIToolbar = ({
 									if (
 										e.key === "Enter" &&
 										(e.metaKey || e.ctrlKey) &&
+										!(e.metaKey && e.ctrlKey) &&
 										!e.shiftKey &&
 										!e.altKey &&
 										!aiLoading &&
diff --git a/tests/ai-toolbar.test.ts b/tests/ai-toolbar.test.ts
index f25a282..567555c 100644
--- a/tests/ai-toolbar.test.ts
+++ b/tests/ai-toolbar.test.ts
@@ -506,6 +506,24 @@ describe("AI toolbar paste capture", () => {
 		expect(onAiCreate).not.toHaveBeenCalled();
 	});
 
+	test("Mod+Enter ignores combined Ctrl+Meta modifiers", async () => {
+		const onAiCreate = mock();
+
+		const { textareaProps } = await renderToolbarBoundary({
+			aiPrompt: "Draft a kickoff",
+			onAiCreate,
+		});
+		const event = createTextareaKeydownEvent({
+			ctrlKey: true,
+			metaKey: 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();
 
@@ -683,6 +701,36 @@ describe("AI toolbar paste capture", () => {
 		);
 	});
 
+	test("clipboard fallback reuses the same synthesized file name for identical clipboard content", async () => {
+		const onImagesSelect = mock();
+		const clipboardRead = mock(async () => [
+			{
+				types: ["image/png"],
+				getType: async () => new Blob(["same-image"], { type: "image/png" }),
+			},
+		]);
+
+		(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 () => [