diff --git a/desktop/src/shared/ui/markdown.tsx b/desktop/src/shared/ui/markdown.tsx
index 84fcf0b9b..8dd10b3d5 100644
--- a/desktop/src/shared/ui/markdown.tsx
+++ b/desktop/src/shared/ui/markdown.tsx
@@ -1,4 +1,4 @@
-import { GitPullRequest } from "lucide-react";
+import { CircleDot, GitCommitHorizontal, GitPullRequest } from "lucide-react";
 import * as React from "react";
 import ReactMarkdown, { type Components } from "react-markdown";
 import remarkBreaks from "remark-breaks";
@@ -15,6 +15,12 @@ import remarkMentions from "@/shared/lib/remarkMentions";
 const GITHUB_PR_RE =
   /^https?:\/\/github\.com\/([^/]+)\/([^/]+)\/pull\/(\d+)\/?$/;
 
+const GITHUB_ISSUE_RE =
+  /^https?:\/\/github\.com\/([^/]+)\/([^/]+)\/issues\/(\d+)\/?$/;
+
+const GITHUB_COMMIT_RE =
+  /^https?:\/\/github\.com\/([^/]+)\/([^/]+)\/commit\/([0-9a-f]{7,40})\/?$/;
+
 type MarkdownProps = {
   channelNames?: string[];
   className?: string;
@@ -46,25 +52,50 @@ function createMarkdownComponents(
 
   return {
     a: ({ children, href, ...props }) => {
-      const prMatch = href ? GITHUB_PR_RE.exec(href) : null;
-      if (prMatch) {
-        const [, owner, repo, number] = prMatch;
-        return (
-          <a
-            {...props}
-            className="relative inline-flex items-center gap-1 rounded-md bg-primary/10 px-1.5 py-0.5 text-sm font-medium text-primary no-underline transition-colors hover:bg-primary/20"
-            href={href}
-            rel="noreferrer"
-            target="_blank"
-          >
-            <span className="pointer-events-none select-none inline-flex items-center gap-1" aria-hidden="true">
-              <GitPullRequest className="size-3.5" />
-              {owner}/{repo}#{number}
-            </span>
-            <span className="absolute w-0 overflow-hidden whitespace-nowrap">{href}</span>
-          </a>
-        );
+      if (href) {
+        let Icon: React.ComponentType<{ className?: string }> | null = null;
+        let label: string | null = null;
+
+        const prMatch = GITHUB_PR_RE.exec(href);
+        if (prMatch) {
+          const [, owner, repo, number] = prMatch;
+          Icon = GitPullRequest;
+          label = `${owner}/${repo}#${number}`;
+        }
+
+        const issueMatch = !Icon ? GITHUB_ISSUE_RE.exec(href) : null;
+        if (issueMatch) {
+          const [, owner, repo, number] = issueMatch;
+          Icon = CircleDot;
+          label = `${owner}/${repo}#${number}`;
+        }
+
+        const commitMatch = !Icon ? GITHUB_COMMIT_RE.exec(href) : null;
+        if (commitMatch) {
+          const [, owner, repo, sha] = commitMatch;
+          Icon = GitCommitHorizontal;
+          label = `${owner}/${repo}@${sha.slice(0, 7)}`;
+        }
+
+        if (Icon && label) {
+          return (
+            <a
+              {...props}
+              className="relative inline-flex items-center gap-1 rounded-md bg-primary/10 px-1.5 py-0.5 text-sm font-medium text-primary no-underline transition-colors hover:bg-primary/20"
+              href={href}
+              rel="noreferrer"
+              target="_blank"
+            >
+              <span className="pointer-events-none select-none inline-flex items-center gap-1" aria-hidden="true">
+                <Icon className="size-3.5" />
+                {label}
+              </span>
+              <span className="absolute w-0 overflow-hidden whitespace-nowrap">{href}</span>
+            </a>
+          );
+        }
       }
+
       return (
         <a
           {...props}
diff --git a/desktop/tests/e2e/smart-links.spec.ts b/desktop/tests/e2e/smart-links.spec.ts
index 8030492f6..f0f44e441 100644
--- a/desktop/tests/e2e/smart-links.spec.ts
+++ b/desktop/tests/e2e/smart-links.spec.ts
@@ -72,6 +72,50 @@ test("selecting a PR chip copies the full URL, not the chip label", async ({
   await expect(visibleLabel).toBeVisible();
 });
 
+test("GitHub issue URL renders as an inline smart chip", async ({ page }) => {
+  const issueUrl = "https://github.com/block/sprout/issues/99";
+  const message = `See ${issueUrl} for context`;
+
+  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();
+
+  const issueChip = lastRow.locator("a", { hasText: "block/sprout#99" });
+  await expect(issueChip).toBeVisible();
+  await expect(issueChip).toHaveAttribute("href", issueUrl);
+  await expect(issueChip.locator("svg")).toBeVisible();
+});
+
+test("GitHub commit URL renders as an inline smart chip", async ({ page }) => {
+  const commitUrl =
+    "https://github.com/block/sprout/commit/abc1234def5678901234567890abcdef12345678";
+  const message = `Reverted in ${commitUrl}`;
+
+  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 show short SHA
+  const commitChip = lastRow.locator("a", {
+    hasText: "block/sprout@abc1234",
+  });
+  await expect(commitChip).toBeVisible();
+  await expect(commitChip).toHaveAttribute("href", commitUrl);
+  await expect(commitChip.locator("svg")).toBeVisible();
+});
+
 test("non-PR GitHub links render as regular links", async ({ page }) => {
   const repoUrl = "https://github.com/block/sprout";
   const message = `Check out ${repoUrl}`;