diff --git a/cli.py b/cli.py
index 8116f5fd..85566756 100755
--- a/cli.py
+++ b/cli.py
@@ -3455,6 +3455,49 @@ class HermesCLI:
         self._background_tasks[task_id] = thread
         thread.start()
 
+    @staticmethod
+    def _try_launch_chrome_debug(port: int, system: str) -> bool:
+        """Try to launch Chrome/Chromium with remote debugging enabled.
+
+        Returns True if a launch command was executed (doesn't guarantee success).
+        """
+        import shutil
+        import subprocess as _sp
+
+        candidates = []
+        if system == "Darwin":
+            # macOS: try common app bundle locations
+            for app in (
+                "/Applications/Google Chrome.app/Contents/MacOS/Google Chrome",
+                "/Applications/Chromium.app/Contents/MacOS/Chromium",
+                "/Applications/Brave Browser.app/Contents/MacOS/Brave Browser",
+                "/Applications/Microsoft Edge.app/Contents/MacOS/Microsoft Edge",
+            ):
+                if os.path.isfile(app):
+                    candidates.append(app)
+        else:
+            # Linux: try common binary names
+            for name in ("google-chrome", "google-chrome-stable", "chromium-browser",
+                         "chromium", "brave-browser", "microsoft-edge"):
+                path = shutil.which(name)
+                if path:
+                    candidates.append(path)
+
+        if not candidates:
+            return False
+
+        chrome = candidates[0]
+        try:
+            _sp.Popen(
+                [chrome, f"--remote-debugging-port={port}"],
+                stdout=_sp.DEVNULL,
+                stderr=_sp.DEVNULL,
+                start_new_session=True,  # detach from terminal
+            )
+            return True
+        except Exception:
+            return False
+
     def _handle_browser_command(self, cmd: str):
         """Handle /browser connect|disconnect|status — manage live Chrome CDP connection."""
         import platform as _plat
@@ -3471,8 +3514,6 @@ class HermesCLI:
             connect_parts = cmd.strip().split(None, 2)  # ["/browser", "connect", "ws://..."]
             cdp_url = connect_parts[2].strip() if len(connect_parts) > 2 else _DEFAULT_CDP
 
-            os.environ["BROWSER_CDP_URL"] = cdp_url
-
             # Clear any existing browser sessions so the next tool call uses the new backend
             try:
                 from tools.browser_tool import cleanup_all_browsers
@@ -3481,38 +3522,68 @@ class HermesCLI:
                 pass
 
             print()
-            print("🌐 Browser connected to live Chrome via CDP")
-            print(f"   Endpoint: {cdp_url}")
-            print()
 
-            # Platform-specific launch instructions
-            sys_name = _plat.system()
-            if sys_name == "Darwin":
-                chrome_cmd = '/Applications/Google\\ Chrome.app/Contents/MacOS/Google\\ Chrome --remote-debugging-port=9222'
-            elif sys_name == "Windows":
-                chrome_cmd = 'chrome.exe --remote-debugging-port=9222'
-            else:
-                chrome_cmd = "google-chrome --remote-debugging-port=9222"
-
-            print("   If Chrome isn't running with remote debugging yet:")
-            print(f"   $ {chrome_cmd}")
-            print()
-
-            # Quick connectivity test
+            # Extract port for connectivity checks
             _port = 9222
             try:
                 _port = int(cdp_url.rsplit(":", 1)[-1].split("/")[0])
             except (ValueError, IndexError):
                 pass
+
+            # Check if Chrome is already listening on the debug port
+            import socket
+            _already_open = False
             try:
-                import socket
                 s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
                 s.settimeout(1)
                 s.connect(("127.0.0.1", _port))
                 s.close()
-                print(f"   ✓ Port {_port} is open — Chrome is reachable")
+                _already_open = True
             except (OSError, socket.timeout):
-                print(f"   ⚠ Port {_port} is not open — launch Chrome with the command above first")
+                pass
+
+            if _already_open:
+                print(f"   ✓ Chrome is already listening on port {_port}")
+            elif cdp_url == _DEFAULT_CDP:
+                # Try to auto-launch Chrome with remote debugging
+                print("   Chrome isn't running with remote debugging — attempting to launch...")
+                _launched = self._try_launch_chrome_debug(_port, _plat.system())
+                if _launched:
+                    # Wait for the port to come up
+                    import time as _time
+                    for _wait in range(10):
+                        try:
+                            s = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
+                            s.settimeout(1)
+                            s.connect(("127.0.0.1", _port))
+                            s.close()
+                            _already_open = True
+                            break
+                        except (OSError, socket.timeout):
+                            _time.sleep(0.5)
+                    if _already_open:
+                        print(f"   ✓ Chrome launched and listening on port {_port}")
+                    else:
+                        print(f"   ⚠ Chrome launched but port {_port} isn't responding yet")
+                        print("     You may need to close existing Chrome windows first and retry")
+                else:
+                    print(f"   ⚠ Could not auto-launch Chrome")
+                    # Show manual instructions as fallback
+                    sys_name = _plat.system()
+                    if sys_name == "Darwin":
+                        chrome_cmd = 'open -a "Google Chrome" --args --remote-debugging-port=9222'
+                    elif sys_name == "Windows":
+                        chrome_cmd = 'chrome.exe --remote-debugging-port=9222'
+                    else:
+                        chrome_cmd = "google-chrome --remote-debugging-port=9222"
+                    print(f"     Launch Chrome manually: {chrome_cmd}")
+            else:
+                print(f"   ⚠ Port {_port} is not reachable at {cdp_url}")
+
+            os.environ["BROWSER_CDP_URL"] = cdp_url
+            print()
+            print("🌐 Browser connected to live Chrome via CDP")
+            print(f"   Endpoint: {cdp_url}")
             print()
 
             # Inject context message so the model knows