diff --git a/src/components/ai-toolbar.tsx b/src/components/ai-toolbar.tsx
index 01c7ae9..2440ee4 100644
--- a/src/components/ai-toolbar.tsx
+++ b/src/components/ai-toolbar.tsx
@@ -310,6 +310,8 @@ export const AIToolbar = ({
 									if (
 										e.key === "Enter" &&
 										(e.metaKey || e.ctrlKey) &&
+										!aiLoading &&
+										canUseAi &&
 										(aiPrompt.trim() || hasImages)
 									) {
 										e.preventDefault();
diff --git a/src/lib/multi-image.ts b/src/lib/multi-image.ts
index 1b5e5e3..df63f8a 100644
--- a/src/lib/multi-image.ts
+++ b/src/lib/multi-image.ts
@@ -8,14 +8,15 @@
 
 /**
  * Returns a stable deduplication key for a File.
- * Key = `name:size` — cheap, deterministic, and catches re-selections of the
- * exact same file (same name *and* same byte count).
+ * Key = `name:size:lastModified` — cheap, deterministic, and catches
+ * re-selections of the exact same file while keeping clipboard fallback files
+ * distinct when they share a generated name and byte size.
  *
- * Two different files that happen to share a name but have different content
- * will have different sizes and therefore different keys.
+ * Two different files that happen to share a generated fallback name but have
+ * different timestamps will not collapse to the same key.
  */
 export function imageFileKey(file: File): string {
-	return `${file.name}:${file.size}`;
+	return `${file.name}:${file.size}:${file.lastModified}`;
 }
 
 /**
diff --git a/tests/ai-toolbar.test.ts b/tests/ai-toolbar.test.ts
index ac10ce7..a8f72b8 100644
--- a/tests/ai-toolbar.test.ts
+++ b/tests/ai-toolbar.test.ts
@@ -488,6 +488,30 @@ describe("AI toolbar paste capture", () => {
 		expect(onAiCreate).toHaveBeenCalledTimes(1);
 	});
 
+	test("Mod+Enter does not trigger AI generation while loading", async () => {
+		const onAiCreate = mock();
+
+		const { textareaProps } = await renderToolbarBoundary({
+			aiPrompt: "Draft a kickoff",
+			aiLoading: true,
+			onAiCreate,
+		});
+		const event = createTextareaKeydownEvent({ ctrlKey: true });
+
+		textareaProps.onKeyDown?.(event);
+
+		expect(event.preventDefault).not.toHaveBeenCalled();
+		expect(onAiCreate).not.toHaveBeenCalled();
+	});
+
+	test("AI unavailable state removes the composer so generate shortcuts are not exposed", async () => {
+		const markup = await renderToolbarMarkup({ aiEnabled: false });
+
+		expect(markup).toContain("AI integrations are unavailable");
+		expect(markup).not.toContain("Type or paste event details...");
+		expect(markup).not.toContain("Generate event");
+	});
+
 	test("Shift+Mod+A opens the image picker when the composer is idle", async () => {
 		const { textareaProps, imageTriggerOpen } = await renderToolbarBoundary();
 		const ctrlEvent = createTextareaKeydownEvent({
diff --git a/tests/multi-image.test.ts b/tests/multi-image.test.ts
index 9ea948a..524d945 100644
--- a/tests/multi-image.test.ts
+++ b/tests/multi-image.test.ts
@@ -13,35 +13,74 @@ import {
 
 describe("imageFileKey – stable identity for dedup", () => {
 	test("returns a string combining name and size", () => {
-		const file = new File(["hello"], "flyer.png", { type: "image/png" });
+		const file = new File(["hello"], "flyer.png", {
+			type: "image/png",
+			lastModified: 123,
+		});
 		const key = imageFileKey(file);
 		expect(typeof key).toBe("string");
 		expect(key).toContain("flyer.png");
 		expect(key).toContain(String(file.size));
+		expect(key).toContain(String(file.lastModified));
 	});
 
-	test("two files with the same name and size produce the same key", () => {
-		const a = new File(["hello"], "a.png", { type: "image/png" });
-		const b = new File(["hello"], "a.png", { type: "image/png" });
+	test("two files with the same name, size, and lastModified produce the same key", () => {
+		const a = new File(["hello"], "a.png", {
+			type: "image/png",
+			lastModified: 123,
+		});
+		const b = new File(["hello"], "a.png", {
+			type: "image/png",
+			lastModified: 123,
+		});
 		expect(imageFileKey(a)).toBe(imageFileKey(b));
 	});
 
 	test("two files with the same name but different content produce different keys", () => {
-		const a = new File(["hello"], "a.png", { type: "image/png" });
-		const b = new File(["hello world"], "a.png", { type: "image/png" });
+		const a = new File(["hello"], "a.png", {
+			type: "image/png",
+			lastModified: 123,
+		});
+		const b = new File(["hello world"], "a.png", {
+			type: "image/png",
+			lastModified: 123,
+		});
 		expect(imageFileKey(a)).not.toBe(imageFileKey(b));
 	});
 
 	test("two files with different names but same content produce different keys", () => {
-		const a = new File(["hello"], "a.png", { type: "image/png" });
-		const b = new File(["hello"], "b.png", { type: "image/png" });
+		const a = new File(["hello"], "a.png", {
+			type: "image/png",
+			lastModified: 123,
+		});
+		const b = new File(["hello"], "b.png", {
+			type: "image/png",
+			lastModified: 123,
+		});
+		expect(imageFileKey(a)).not.toBe(imageFileKey(b));
+	});
+
+	test("clipboard fallback files with the same fallback name and size stay distinct when lastModified differs", () => {
+		const a = new File(["abcd"], "clipboard-image", {
+			type: "image/png",
+			lastModified: 100,
+		});
+		const b = new File(["wxyz"], "clipboard-image", {
+			type: "image/png",
+			lastModified: 101,
+		});
+
+		expect(a.size).toBe(b.size);
 		expect(imageFileKey(a)).not.toBe(imageFileKey(b));
 	});
 });
 
 describe("appendImagesDeduped – append with deduplication", () => {
-	const makeFile = (name: string, content = "data") =>
-		new File([content], name, { type: "image/png" });
+	const makeFile = (
+		name: string,
+		content = "data",
+		lastModified = 123,
+	) => new File([content], name, { type: "image/png", lastModified });
 
 	test("appends new files to an empty list", () => {
 		const result = appendImagesDeduped([], [makeFile("a.png")]);
@@ -100,4 +139,18 @@ describe("appendImagesDeduped – append with deduplication", () => {
 		expect(result).toHaveLength(2);
 		expect(result.map((f) => f.name)).toEqual(["a.png", "b.png"]);
 	});
+
+	test("keeps distinct clipboard fallback files that share the same name and byte size", () => {
+		const existing: File[] = [];
+		const incoming = [
+			makeFile("clipboard-image", "abcd", 100),
+			makeFile("clipboard-image", "wxyz", 101),
+		];
+
+		const result = appendImagesDeduped(existing, incoming);
+
+		expect(result).toHaveLength(2);
+		expect(result[0].lastModified).toBe(100);
+		expect(result[1].lastModified).toBe(101);
+	});
 });