diff --git a/tests/ai-toolbar.test.ts b/tests/ai-toolbar.test.ts
index aa2e4f6..ba8fe03 100644
--- a/tests/ai-toolbar.test.ts
+++ b/tests/ai-toolbar.test.ts
@@ -1,10 +1,7 @@
 import { afterEach, beforeEach, describe, expect, mock, test } from "bun:test";
-import { readFileSync } from "node:fs";
 import * as React from "react";
 import { renderToStaticMarkup } from "react-dom/server";
 
-const readToolbarSource = () => readFileSync("src/components/ai-toolbar.tsx", "utf8");
-
 type AIToolbarProps = {
 	adminAiEnabled: boolean;
 	aiEnabled: boolean;
@@ -128,7 +125,12 @@ const renderToolbar = async (overrides: Partial<AIToolbarProps> = {}) => {
 
 const renderToolbarMarkup = async (
 	overrides: Partial<AIToolbarProps> = {},
+	{ isMobile = false }: { isMobile?: boolean } = {},
 ) => {
+	mock.module("@/hooks/use-mobile", () => ({
+		useIsMobile: () => isMobile,
+	}));
+
 	const { AIToolbar } = await import("@/components/ai-toolbar");
 
 	return renderToStaticMarkup(
@@ -136,6 +138,22 @@ const renderToolbarMarkup = async (
 	);
 };
 
+const escapeForRegex = (value: string) =>
+	value.replace(/[.*+?^${}()|[\]\\]/g, "\\$&");
+
+const getButtonOpeningTag = (markup: string, label: string) => {
+	const buttonMatch = markup.match(
+		new RegExp(
+			`<button\\b[^>]*>(?:(?!<\\/button>)[\\s\\S])*?${escapeForRegex(label)}(?:(?!<\\/button>)[\\s\\S])*?<\\/button>`,
+		),
+	);
+	const openingTagMatch = buttonMatch?.[0].match(/^<button\b[^>]*>/);
+
+	expect(openingTagMatch).toBeDefined();
+
+	return openingTagMatch![0];
+};
+
 const renderToolbarBoundary = async (
 	overrides: Partial<AIToolbarProps> = {},
 ) => {
@@ -160,27 +178,29 @@ const renderToolbarBoundary = async (
 };
 
 describe("AI toolbar layout contracts", () => {
-	test("desktop composer uses a 70/30 split driven by the isMobile branch", () => {
-		const source = readToolbarSource();
+	test("desktop composer renders a 70/30 split while mobile stays single-column", async () => {
+		const desktopMarkup = await renderToolbarMarkup();
+		const mobileMarkup = await renderToolbarMarkup({}, { isMobile: true });
 
-		expect(source).toContain("isMobile");
-		expect(source).toContain('? "grid gap-3"');
-		expect(source).toContain(
-			': "grid gap-3 grid-cols-[minmax(0,0.7fr)_minmax(0,0.3fr)]"',
+		expect(desktopMarkup).toContain(
+			"grid gap-3 grid-cols-[minmax(0,0.7fr)_minmax(0,0.3fr)]",
 		);
-		expect(source).not.toContain(
-			': "grid gap-3 grid-cols-[minmax(0,1fr)_minmax(0,1fr)]"',
+		expect(desktopMarkup).not.toContain(
+			"grid gap-3 grid-cols-[minmax(0,1fr)_minmax(0,1fr)]",
+		);
+		expect(mobileMarkup).not.toContain(
+			"grid-cols-[minmax(0,0.7fr)_minmax(0,0.3fr)]",
 		);
 	});
 
-	test("example prompts render as a two-column masonry-style cluster below the textarea", () => {
-		const source = readToolbarSource();
+	test("example prompts render as a masonry-style cluster below the textarea", async () => {
+		const markup = await renderToolbarMarkup();
 
-		expect(source).toContain("Try:");
-		expect(source).toContain('className="columns-2 gap-2"');
-		expect(source).toContain('className="mb-2 break-inside-avoid"');
-		expect(source).toContain(
-			'className="h-auto w-full justify-start text-left whitespace-normal rounded-2xl px-3 py-2 text-[11px] leading-relaxed"',
+		expect(markup).toContain("Try:");
+		expect(markup).toContain('class="columns-2 gap-2"');
+		expect(markup).toContain('class="mb-2 break-inside-avoid"');
+		expect(markup).toContain(
+			"h-auto w-full justify-start text-left whitespace-normal rounded-2xl px-3 py-2 text-[11px] leading-relaxed",
 		);
 	});
 
@@ -195,15 +215,19 @@ describe("AI toolbar layout contracts", () => {
 		);
 	});
 
-	test("attachment previews stack one per row instead of rendering a horizontal strip or multi-column gallery", () => {
-		const source = readToolbarSource();
-		const previewGridClassNames = [...source.matchAll(
-			/className="([^"]*\bmt-3\b[^"]*\bgrid\b[^"]*\bgap-2\b[^"]*)"/g,
+	test("attachment previews render in a stacked grid instead of a multi-column strip", async () => {
+		const markup = await renderToolbarMarkup({
+			imagePreviews: ["blob:first", "blob:second"],
+		});
+		const previewGridClassNames = [...markup.matchAll(
+			/class="([^"]*\bmt-3\b[^"]*\bgrid\b[^"]*\bgap-2\b[^"]*)"/g,
 		)].map(([, className]) => className);
 		const multiColumnPreviewPattern =
 			/(?:^|\s)(?:[a-z]+:)*(?:grid-cols-(?:\[[^\]]+\]|\S+)|grid-flow-col|auto-cols-(?:\[[^\]]+\]|\S+)|columns-(?:\[[^\]]+\]|\S+)|overflow-x-auto|flex-row)/;
 
-		expect(source).toContain('className="mt-3 grid gap-2"');
+		expect(markup).toContain('class="mt-3 grid gap-2"');
+		expect(markup).toContain("Attached image 1");
+		expect(markup).toContain("Attached image 2");
 		expect(previewGridClassNames).toHaveLength(1);
 		expect(previewGridClassNames[0]).not.toMatch(multiColumnPreviewPattern);
 	});
@@ -255,6 +279,43 @@ describe("AI toolbar state rendering", () => {
 		expect(markup).toContain("Updated just now");
 		expect(markup).toContain("Dismiss AI summary");
 	});
+
+	test("Summarize only appears when there are events to summarize", async () => {
+		const emptyMarkup = await renderToolbarMarkup({ events: [] });
+		const populatedMarkup = await renderToolbarMarkup({
+			events: [{ id: "event-1" }],
+		});
+
+		expect(emptyMarkup).not.toContain("Summarize");
+		expect(populatedMarkup).toContain("Summarize");
+	});
+
+	test("Generate event stays disabled while loading or when both prompt and images are absent", async () => {
+		const emptyMarkup = await renderToolbarMarkup();
+		const loadingMarkup = await renderToolbarMarkup({
+			aiLoading: true,
+			aiPrompt: "Draft a kickoff",
+		});
+		const promptMarkup = await renderToolbarMarkup({
+			aiPrompt: "Draft a kickoff",
+		});
+		const imageMarkup = await renderToolbarMarkup({
+			imagePreviews: ["blob:first"],
+		});
+
+		expect(getButtonOpeningTag(emptyMarkup, "Generate event")).toContain(
+			" disabled=\"\"",
+		);
+		expect(getButtonOpeningTag(loadingMarkup, "Generating...")).toContain(
+			" disabled=\"\"",
+		);
+		expect(getButtonOpeningTag(promptMarkup, "Generate event")).not.toContain(
+			" disabled=",
+		);
+		expect(getButtonOpeningTag(imageMarkup, "Generate event")).not.toContain(
+			" disabled=",
+		);
+	});
 });
 
 describe("AI toolbar paste capture", () => {