diff --git a/src/components/ai-toolbar.tsx b/src/components/ai-toolbar.tsx
index 2440ee4..e7622f9 100644
--- a/src/components/ai-toolbar.tsx
+++ b/src/components/ai-toolbar.tsx
@@ -40,6 +40,15 @@ function useOs(): Os {
 	return os;
 }
 
+function createClipboardFallbackFile(blob: Blob, index: number): File {
+	const createdAt = Date.now() + index;
+	const extension = blob.type.split("/")[1] || "png";
+	return new File([blob], `clipboard-image-${createdAt}.${extension}`, {
+		type: blob.type,
+		lastModified: createdAt,
+	});
+}
+
 // ─── Shared shortcuts list (rendered in both HoverCard and Popover) ───────────
 
 function ShortcutsList({ os }: { os: Os }) {
@@ -220,9 +229,7 @@ export const AIToolbar = ({
 					for (const mimeType of typesToTry) {
 						try {
 							const blob = await clipboardItem.getType(mimeType);
-							files.push(
-								new File([blob], "clipboard-image", { type: mimeType }),
-							);
+							files.push(createClipboardFallbackFile(blob, files.length));
 							break; // got this item, move to next clipboardItem
 						} catch {
 							// NotFoundError — type not present, try next
@@ -310,6 +317,8 @@ export const AIToolbar = ({
 									if (
 										e.key === "Enter" &&
 										(e.metaKey || e.ctrlKey) &&
+										!e.shiftKey &&
+										!e.altKey &&
 										!aiLoading &&
 										canUseAi &&
 										(aiPrompt.trim() || hasImages)
diff --git a/tests/ai-toolbar.test.ts b/tests/ai-toolbar.test.ts
index a8f72b8..f25a282 100644
--- a/tests/ai-toolbar.test.ts
+++ b/tests/ai-toolbar.test.ts
@@ -488,6 +488,24 @@ describe("AI toolbar paste capture", () => {
 		expect(onAiCreate).toHaveBeenCalledTimes(1);
 	});
 
+	test("Mod+Enter ignores extra modifiers so Shift+Ctrl+Enter does not generate", async () => {
+		const onAiCreate = mock();
+
+		const { textareaProps } = await renderToolbarBoundary({
+			aiPrompt: "Draft a kickoff",
+			onAiCreate,
+		});
+		const event = createTextareaKeydownEvent({
+			ctrlKey: true,
+			shiftKey: 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();
 
@@ -630,6 +648,41 @@ describe("AI toolbar paste capture", () => {
 		expect(onImagesSelect.mock.calls[0]?.[0][0]?.type).toBe("image/png");
 	});
 
+	test("clipboard fallback creates distinct files for same-sized clipboard images", async () => {
+		const onImagesSelect = mock();
+		const clipboardRead = mock(async () => [
+			{
+				types: ["image/png"],
+				getType: async () => new Blob(["abcd"], { type: "image/png" }),
+			},
+			{
+				types: ["image/png"],
+				getType: async () => new Blob(["wxyz"], { 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 }),
+		);
+
+		expect(onImagesSelect).toHaveBeenCalledTimes(1);
+		expect(onImagesSelect.mock.calls[0]?.[0]).toHaveLength(2);
+		expect(onImagesSelect.mock.calls[0]?.[0][0]?.name).not.toBe(
+			onImagesSelect.mock.calls[0]?.[0][1]?.name,
+		);
+		expect(onImagesSelect.mock.calls[0]?.[0][0]?.size).toBe(
+			onImagesSelect.mock.calls[0]?.[0][1]?.size,
+		);
+	});
+
 	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 () => [