diff --git a/e2e-tests/fixtures/write-index-2.md b/e2e-tests/fixtures/write-index-2.md
new file mode 100644
index 0000000..eca1b5a
--- /dev/null
+++ b/e2e-tests/fixtures/write-index-2.md
@@ -0,0 +1,15 @@
+OK, I'm going to do some writing now...
+
+<dyad-write path="src/pages/Index.tsx" description="write-description">
+const Index = () => {
+  return (
+    <div>
+        Testing:write-index(2)!
+    </div>
+  );
+};
+
+export default Index;
+</dyad-write>
+
+And it's done!
diff --git a/e2e-tests/helpers/test_helper.ts b/e2e-tests/helpers/test_helper.ts
index b63640a..bcd2545 100644
--- a/e2e-tests/helpers/test_helper.ts
+++ b/e2e-tests/helpers/test_helper.ts
@@ -73,10 +73,18 @@ class PageObject {
     await this.getRetryButton().click();
   }
 
+  async clickUndo() {
+    await this.getUndoButton().click();
+  }
+
   private getRetryButton() {
     return this.page.getByRole("button", { name: "Retry" });
   }
 
+  private getUndoButton() {
+    return this.page.getByRole("button", { name: "Undo" });
+  }
+
   async sendPrompt(prompt: string) {
     await this.page
       .getByRole("textbox", { name: "Ask Dyad to build..." })
@@ -84,7 +92,7 @@ class PageObject {
     await this.page
       .getByRole("textbox", { name: "Ask Dyad to build..." })
       .fill(prompt);
-    await this.page.getByRole("button", { name: "Start new chat" }).click();
+    await this.page.getByRole("button", { name: "Send message" }).click();
     await this.waitForChatCompletion();
   }
 
diff --git a/e2e-tests/undo.spec.ts b/e2e-tests/undo.spec.ts
new file mode 100644
index 0000000..d4ab487
--- /dev/null
+++ b/e2e-tests/undo.spec.ts
@@ -0,0 +1,25 @@
+import { test } from "./helpers/test_helper";
+import { expect } from "@playwright/test";
+
+test("undo", async ({ po }) => {
+  await po.setUp({ autoApprove: true });
+  await po.sendPrompt("tc=write-index");
+  await po.sendPrompt("tc=write-index-2");
+
+  const iframe = po.getPreviewIframeElement();
+  await expect(
+    iframe.contentFrame().getByText("Testing:write-index(2)!"),
+  ).toBeVisible({
+    // This can be pretty slow because it's waiting for the app to build.
+    timeout: 15_000,
+  });
+
+  await po.clickUndo();
+
+  await expect(
+    iframe.contentFrame().getByText("Testing:write-index!"),
+  ).toBeVisible({
+    // Also, could be slow.
+    timeout: 15_000,
+  });
+});
diff --git a/src/components/chat/ChatInput.tsx b/src/components/chat/ChatInput.tsx
index 1436fc0..9086261 100644
--- a/src/components/chat/ChatInput.tsx
+++ b/src/components/chat/ChatInput.tsx
@@ -333,6 +333,7 @@ export function ChatInput({ chatId }: { chatId?: number }) {
                 onClick={handleSubmit}
                 disabled={!inputValue.trim() && attachments.length === 0}
                 className="px-2 py-2 mt-1 mr-2 hover:bg-(--background-darkest) text-(--sidebar-accent-fg) rounded-lg disabled:opacity-50"
+                title="Send message"
               >
                 <SendIcon size={20} />
               </button>
diff --git a/src/components/chat/HomeChatInput.tsx b/src/components/chat/HomeChatInput.tsx
index eca8c14..87f115a 100644
--- a/src/components/chat/HomeChatInput.tsx
+++ b/src/components/chat/HomeChatInput.tsx
@@ -139,7 +139,7 @@ export function HomeChatInput({
                 onClick={handleCustomSubmit}
                 disabled={!inputValue.trim() && attachments.length === 0}
                 className="px-2 py-2 mt-1 mr-2 hover:bg-(--background-darkest) text-(--sidebar-accent-fg) rounded-lg disabled:opacity-50"
-                title="Start new chat"
+                title="Send message"
               >
                 <SendIcon size={20} />
               </button>