diff --git a/onionshare/__init__.py b/onionshare/__init__.py
index 29bc0ed4..006ed4c0 100644
--- a/onionshare/__init__.py
+++ b/onionshare/__init__.py
@@ -156,7 +156,7 @@ def main(cwd=None):
         app = OnionShare(debug, local_only, stay_open, transparent_torification, stealth)
         app.choose_port()
         app.start_onion_service()
-    except (TorTooOld, TorErrorInvalidSetting, TorErrorAutomatic, TorErrorSocketPort, TorErrorSocketFile, TorErrorMissingPassword, TorErrorUnreadableCookieFile, TorErrorAuthError, TorErrorProtocolError, BundledTorNotSupported) as e:
+    except (TorTooOld, TorErrorInvalidSetting, TorErrorAutomatic, TorErrorSocketPort, TorErrorSocketFile, TorErrorMissingPassword, TorErrorUnreadableCookieFile, TorErrorAuthError, TorErrorProtocolError, BundledTorNotSupported, BundledTorTimeout) as e:
         sys.exit(e.args[0])
     except KeyboardInterrupt:
         print("")
diff --git a/onionshare/onion.py b/onionshare/onion.py
index 8ac03dd6..be10743f 100644
--- a/onionshare/onion.py
+++ b/onionshare/onion.py
@@ -93,6 +93,12 @@ class BundledTorNotSupported(Exception):
     but it's not supported on that platform, or in dev mode.
     """
 
+class BundledTorTimeout(Exception):
+    """
+    This exception is raised if onionshare is set to use the bundled Tor binary,
+    but Tor doesn't finish connecting promptly.
+    """
+
 class Onion(object):
     """
     Onion is an abstraction layer for connecting to the Tor control port and
@@ -165,6 +171,7 @@ class Onion(object):
             open(self.tor_torrc, 'w').write(torrc_template)
 
             # Open tor in a subprocess, wait for the controller to start
+            start_ts = time.time()
             self.tor_proc = subprocess.Popen([self.tor_path, '-f', self.tor_torrc], stdout=subprocess.PIPE, stderr=subprocess.PIPE)
             time.sleep(0.2)
 
@@ -190,6 +197,12 @@ class Onion(object):
                     break
                 time.sleep(0.2)
 
+                # Timeout after 10 seconds
+                if time.time() - start_ts > 10:
+                    print("")
+                    self.tor_proc.terminate()
+                    raise BundledTorTimeout(strings._('settings_error_bundled_tor_timeout'))
+
         elif self.settings.get('connection_type') == 'automatic':
             # Automatically try to guess the right way to connect to Tor Browser
 
diff --git a/onionshare_gui/__init__.py b/onionshare_gui/__init__.py
index 5e2617da..bc15f8c9 100644
--- a/onionshare_gui/__init__.py
+++ b/onionshare_gui/__init__.py
@@ -185,7 +185,7 @@ class OnionShareGui(QtWidgets.QMainWindow):
                 self.app.start_onion_service(bundled_tor_func)
                 self.starting_server_step2.emit()
 
-            except (onionshare.onion.TorTooOld, onionshare.onion.TorErrorInvalidSetting, onionshare.onion.TorErrorAutomatic, onionshare.onion.TorErrorSocketPort, onionshare.onion.TorErrorSocketFile, onionshare.onion.TorErrorMissingPassword, onionshare.onion.TorErrorUnreadableCookieFile, onionshare.onion.TorErrorAuthError, onionshare.onion.TorErrorProtocolError) as e:
+            except (onionshare.onion.TorTooOld, onionshare.onion.TorErrorInvalidSetting, onionshare.onion.TorErrorAutomatic, onionshare.onion.TorErrorSocketPort, onionshare.onion.TorErrorSocketFile, onionshare.onion.TorErrorMissingPassword, onionshare.onion.TorErrorUnreadableCookieFile, onionshare.onion.TorErrorAuthError, onionshare.onion.TorErrorProtocolError, onionshare.onion.BundledTorTimeout) as e:
                 self.starting_server_error.emit(e.args[0])
                 return
 
diff --git a/onionshare_gui/settings_dialog.py b/onionshare_gui/settings_dialog.py
index 74c70391..46c0b7e3 100644
--- a/onionshare_gui/settings_dialog.py
+++ b/onionshare_gui/settings_dialog.py
@@ -285,21 +285,27 @@ class SettingsDialog(QtWidgets.QDialog):
         """
         settings = self.settings_from_fields()
 
+        def bundled_setup():
+            self.tor_status.show()
+            self.test_button.setEnabled(False)
+            self.save_button.setEnabled(False)
+            self.cancel_button.setEnabled(False)
+
+        def bundled_cleanup():
+            self.tor_status.hide()
+            self.test_button.setEnabled(True)
+            self.save_button.setEnabled(True)
+            self.cancel_button.setEnabled(True)
+
         try:
             # Show Tor connection status if connection type is bundled tor
             if settings.get('connection_type') == 'bundled':
-                self.tor_status.show()
-                self.test_button.setEnabled(False)
-                self.save_button.setEnabled(False)
-                self.cancel_button.setEnabled(False)
+                bundled_setup()
                 def bundled_tor_func(message):
                     self.tor_status.setText('<strong>{}</strong><br>{}'.format(strings._('connecting_to_tor', True), message))
                     self.qtapp.processEvents()
                     if 'Done' in message:
-                        self.tor_status.hide()
-                        self.test_button.setEnabled(True)
-                        self.save_button.setEnabled(True)
-                        self.cancel_button.setEnabled(True)
+                        bundled_cleanup()
             else:
                 bundled_tor_func = None
 
@@ -308,8 +314,13 @@ class SettingsDialog(QtWidgets.QDialog):
             # If an exception hasn't been raised yet, the Tor settings work
             Alert(strings._('settings_test_success', True).format(onion.tor_version, onion.supports_ephemeral, onion.supports_stealth))
 
-        except (TorErrorInvalidSetting, TorErrorAutomatic, TorErrorSocketPort, TorErrorSocketFile, TorErrorMissingPassword, TorErrorUnreadableCookieFile, TorErrorAuthError, TorErrorProtocolError, BundledTorNotSupported) as e:
+            # Clean up
+            onion.cleanup()
+
+        except (TorErrorInvalidSetting, TorErrorAutomatic, TorErrorSocketPort, TorErrorSocketFile, TorErrorMissingPassword, TorErrorUnreadableCookieFile, TorErrorAuthError, TorErrorProtocolError, BundledTorNotSupported, BundledTorTimeout) as e:
             Alert(e.args[0], QtWidgets.QMessageBox.Warning)
+            if settings.get('connection_type') == 'bundled':
+                bundled_cleanup()
 
     def save_clicked(self):
         """
diff --git a/share/locale/en.json b/share/locale/en.json
index d4743cf4..4eb6ec6e 100644
--- a/share/locale/en.json
+++ b/share/locale/en.json
@@ -86,6 +86,7 @@
     "settings_error_missing_password": "Connected to Tor controller, but it requires a password to authenticate.",
     "settings_error_unreadable_cookie_file": "Connected to Tor controller, but can't authenticate because your password may be wrong, and your user doesn't have permission to read the cookie file.",
     "settings_error_bundled_tor_not_supported": "Bundled Tor is only supported in Windows and macOS. It's not supported when not using developer mode or the command line interface.",
+    "settings_error_bundled_tor_timeout": "Connecting to Tor is taking too long. Make sure you're online and your clock is accurate, then try again.",
     "settings_test_success": "Congratulations, OnionShare can connect to the Tor controller.\n\nTor version: {}\nSupports ephemeral onion services: {}\nSupports stealth onion services: {}",
     "error_tor_protocol_error": "Error talking to the Tor controller.\nIf you're using Whonix, check out https://www.whonix.org/wiki/onionshare to make OnionShare work.",
     "connecting_to_tor": "Connecting to the Tor network"