diff --git a/desktop/playwright.config.ts b/desktop/playwright.config.ts
index 3ed95fd51..da5e244bc 100644
--- a/desktop/playwright.config.ts
+++ b/desktop/playwright.config.ts
@@ -24,6 +24,7 @@ export default defineConfig({
         "**/channel-browser.spec.ts",
         "**/messaging.spec.ts",
         "**/mentions.spec.ts",
+        "**/smart-links.spec.ts",
         "**/workflows.spec.ts",
       ],
       use: {
diff --git a/desktop/tests/e2e/smart-links.spec.ts b/desktop/tests/e2e/smart-links.spec.ts
new file mode 100644
index 000000000..e047c604a
--- /dev/null
+++ b/desktop/tests/e2e/smart-links.spec.ts
@@ -0,0 +1,68 @@
+import { expect, test } from "@playwright/test";
+
+import { installMockBridge } from "../helpers/bridge";
+
+test.beforeEach(async ({ page }) => {
+  await installMockBridge(page);
+});
+
+test("GitHub PR URL renders as an inline smart chip", async ({ page }) => {
+  const prUrl = "https://github.com/block/goose2/pull/125";
+  const message = `Check out ${prUrl} for the fix`;
+
+  await page.goto("/");
+  await page.getByTestId("channel-general").click();
+  await expect(page.getByTestId("chat-title")).toHaveText("general");
+
+  const input = page.getByTestId("message-input");
+  await input.fill(message);
+  await page.getByTestId("send-message").click();
+
+  const lastRow = page.getByTestId("message-row").last();
+
+  // The PR link should render as a styled chip with the repo and PR number
+  const prChip = lastRow.locator("a", { hasText: "block/goose2#125" });
+  await expect(prChip).toBeVisible();
+  await expect(prChip).toHaveAttribute("href", prUrl);
+
+  // Should contain the GitPullRequest icon (rendered as an SVG)
+  await expect(prChip.locator("svg")).toBeVisible();
+});
+
+test("GitHub PR chip links open in new tab", async ({ page }) => {
+  const prUrl = "https://github.com/block/sprout/pull/42";
+
+  await page.goto("/");
+  await page.getByTestId("channel-general").click();
+  await expect(page.getByTestId("chat-title")).toHaveText("general");
+
+  const input = page.getByTestId("message-input");
+  await input.fill(prUrl);
+  await page.getByTestId("send-message").click();
+
+  const lastRow = page.getByTestId("message-row").last();
+  const prChip = lastRow.locator("a", { hasText: "block/sprout#42" });
+  await expect(prChip).toHaveAttribute("target", "_blank");
+  await expect(prChip).toHaveAttribute("rel", "noreferrer");
+});
+
+test("non-PR GitHub links render as regular links", async ({ page }) => {
+  const repoUrl = "https://github.com/block/sprout";
+  const message = `Check out ${repoUrl}`;
+
+  await page.goto("/");
+  await page.getByTestId("channel-general").click();
+  await expect(page.getByTestId("chat-title")).toHaveText("general");
+
+  const input = page.getByTestId("message-input");
+  await input.fill(message);
+  await page.getByTestId("send-message").click();
+
+  const lastRow = page.getByTestId("message-row").last();
+
+  // Should render as a normal underlined link, not a chip
+  const link = lastRow.locator("a", { hasText: repoUrl });
+  await expect(link).toBeVisible();
+  // Regular links have underline styling, not the chip background
+  await expect(link.locator("svg")).not.toBeVisible();
+});