diff --git a/apps/desktop/src-electron/main/window.test.ts b/apps/desktop/src-electron/main/window.test.ts
index 1259eb7b..68dfab31 100644
--- a/apps/desktop/src-electron/main/window.test.ts
+++ b/apps/desktop/src-electron/main/window.test.ts
@@ -1,6 +1,10 @@
 import path from "node:path";
 import { describe, expect, it } from "vitest";
-import { resolveRendererDevUrl, resolveWindowIconPath } from "./window";
+import {
+    resolveRendererDevUrl,
+    resolveWindowIconPath,
+    shouldOpenInSystemBrowser,
+} from "./window";
 
 describe("resolveRendererDevUrl", () => {
     it("returns the dev URL for unpackaged builds", () => {
@@ -65,3 +69,21 @@ describe("resolveWindowIconPath", () => {
         ).toBeUndefined();
     });
 });
+
+describe("shouldOpenInSystemBrowser", () => {
+    it("allows website and email links", () => {
+        expect(shouldOpenInSystemBrowser("https://example.com/docs")).toBe(
+            true,
+        );
+        expect(shouldOpenInSystemBrowser("http://localhost:3000")).toBe(true);
+        expect(shouldOpenInSystemBrowser("mailto:team@example.com")).toBe(true);
+    });
+
+    it("blocks app, file, and malformed URLs", () => {
+        expect(shouldOpenInSystemBrowser("neverwrite://clip")).toBe(false);
+        expect(shouldOpenInSystemBrowser("file:///Users/test/note.md")).toBe(
+            false,
+        );
+        expect(shouldOpenInSystemBrowser("not a url")).toBe(false);
+    });
+});
diff --git a/apps/desktop/src-electron/main/window.ts b/apps/desktop/src-electron/main/window.ts
index b0f4be9c..c7efd04b 100644
--- a/apps/desktop/src-electron/main/window.ts
+++ b/apps/desktop/src-electron/main/window.ts
@@ -1,7 +1,7 @@
 import fs from "node:fs";
 import path from "node:path";
 import { fileURLToPath } from "node:url";
-import { app, BrowserWindow, nativeTheme } from "electron";
+import { app, BrowserWindow, nativeTheme, shell } from "electron";
 import { ELECTRON_IPC } from "../shared/ipc";
 import { writeAppLog } from "./appLogger";
 import { removeWindowVaultRoute } from "./shellState";
@@ -44,6 +44,7 @@ function readTrafficLightPosition(
 
 const windowsByLabel = new Map<string, BrowserWindow>();
 const labelsByWebContentsId = new Map<number, string>();
+const SYSTEM_BROWSER_PROTOCOLS = new Set(["http:", "https:", "mailto:"]);
 
 function preloadPath() {
     return fileURLToPath(
@@ -174,6 +175,30 @@ function getOptionalNumber(
         : undefined;
 }
 
+export function shouldOpenInSystemBrowser(url: string) {
+    try {
+        return SYSTEM_BROWSER_PROTOCOLS.has(new URL(url).protocol);
+    } catch {
+        return false;
+    }
+}
+
+function bindExternalWindowOpenHandler(window: BrowserWindow) {
+    window.webContents.setWindowOpenHandler(({ url }) => {
+        if (shouldOpenInSystemBrowser(url)) {
+            void shell.openExternal(url).catch((error: unknown) => {
+                writeAppLog("main", "error", "Failed to open external link", {
+                    url,
+                    error:
+                        error instanceof Error ? error.message : String(error),
+                });
+            });
+        }
+
+        return { action: "deny" };
+    });
+}
+
 function bindWindowLifecycle(label: string, window: BrowserWindow) {
     const webContentsId = window.webContents.id;
     windowsByLabel.set(label, window);
@@ -384,6 +409,7 @@ export function createAppWindow(
         },
     });
 
+    bindExternalWindowOpenHandler(window);
     bindWindowLifecycle(label, window);
 
     const rendererEntry = resolveRendererEntry(search);
diff --git a/apps/desktop/src/features/ai/components/MarkdownContent.test.tsx b/apps/desktop/src/features/ai/components/MarkdownContent.test.tsx
index 23b629e0..fe08ac57 100644
--- a/apps/desktop/src/features/ai/components/MarkdownContent.test.tsx
+++ b/apps/desktop/src/features/ai/components/MarkdownContent.test.tsx
@@ -71,6 +71,23 @@ describe("MarkdownContent", () => {
         ).not.toBeInTheDocument();
     });
 
+    it("renders raw http and https URLs as external links", () => {
+        renderComponent(
+            <MarkdownContent
+                content="Read https://example.com/docs and try http://localhost:3000."
+                pillMetrics={pillMetrics}
+            />,
+        );
+
+        expect(
+            screen.getByRole("link", { name: "https://example.com/docs" }),
+        ).toHaveAttribute("href", "https://example.com/docs");
+        expect(
+            screen.getByRole("link", { name: "http://localhost:3000" }),
+        ).toHaveAttribute("href", "http://localhost:3000");
+        expect(document.body).toHaveTextContent("http://localhost:3000.");
+    });
+
     it("opens relative markdown text file links in a new tab from the context menu", async () => {
         const invokeMock = vi.mocked(invoke);
         invokeMock.mockImplementation(async (command, args) => {
diff --git a/apps/desktop/src/features/ai/components/MarkdownContent.tsx b/apps/desktop/src/features/ai/components/MarkdownContent.tsx
index 80fefc45..62a31989 100644
--- a/apps/desktop/src/features/ai/components/MarkdownContent.tsx
+++ b/apps/desktop/src/features/ai/components/MarkdownContent.tsx
@@ -328,6 +328,34 @@ type InlineContextMenuHandler = (
     reference: string,
 ) => void;
 
+function renderExternalLink(key: number, href: string, label = href) {
+    return (
+        <a
+            key={key}
+            href={href}
+            target="_blank"
+            rel="noopener noreferrer"
+            style={{
+                color: "var(--accent)",
+                whiteSpace: "normal",
+                overflowWrap: "anywhere",
+                wordBreak: "break-word",
+            }}
+            className="underline"
+        >
+            {label}
+        </a>
+    );
+}
+
+function splitTrailingUrlPunctuation(url: string) {
+    const match = /^(.+?)([.,!?;:]*)$/.exec(url);
+    return {
+        href: match?.[1] ?? url,
+        trailing: match?.[2] ?? "",
+    };
+}
+
 function renderInlineMarkdown(
     text: string,
     pillMetrics: ChatPillMetrics,
@@ -337,9 +365,9 @@ function renderInlineMarkdown(
     onFileContextMenu?: InlineContextMenuHandler,
 ): Array<string | ReactElement> {
     const parts: Array<string | ReactElement> = [];
-    // Process: wikilinks, inline code, bold, italic, links, and absolute vault file paths.
+    // Process: wikilinks, inline code, bold, italic, links, raw URLs, and absolute vault file paths.
     const inlineRegex =
-        /(\[\[[^\]]+\]\])|(`[^`]+`)|(\*\*[^*]+\*\*)|(\*[^*]+\*)|(\[[^\]]+\]\([^)]+\))|((?<![\w\u00C0-\u024F])(?:\/)[\w\u00C0-\u024F~.()/-]+(?::\d+|#L\d+)?)/g;
+        /(\[\[[^\]]+\]\])|(`[^`]+`)|(\*\*[^*]+\*\*)|(\*[^*]+\*)|(\[[^\]]+\]\([^)]+\))|(\bhttps?:\/\/[^\s<>"']+)|((?<![\w\u00C0-\u024F])(?:\/)[\w\u00C0-\u024F~.()/-]+(?::\d+|#L\d+)?)/g;
     let lastIndex = 0;
     let match: RegExpExecArray | null;
     let keyIndex = 0;
@@ -592,26 +620,16 @@ function renderInlineMarkdown(
                         />,
                     );
                 } else {
-                    parts.push(
-                        <a
-                            key={key}
-                            href={url}
-                            target="_blank"
-                            rel="noopener noreferrer"
-                            style={{
-                                color: "var(--accent)",
-                                whiteSpace: "normal",
-                                overflowWrap: "anywhere",
-                                wordBreak: "break-word",
-                            }}
-                            className="underline"
-                        >
-                            {linkMatch[1]}
-                        </a>,
-                    );
+                    parts.push(renderExternalLink(key, url, linkMatch[1]));
                 }
             }
         } else if (match[6]) {
+            const { href, trailing } = splitTrailingUrlPunctuation(full);
+            parts.push(renderExternalLink(key, href));
+            if (trailing) {
+                parts.push(trailing);
+            }
+        } else if (match[7]) {
             // Absolute vault file path.
             const filePath = safeDecodeUriComponent(full);
             const excalidrawRef = parseExcalidrawReference(filePath);