diff --git a/onionshare/onion.py b/onionshare/onion.py
index 2f79719b..adfb4dbf 100644
--- a/onionshare/onion.py
+++ b/onionshare/onion.py
@@ -375,6 +375,12 @@ class Onion(object):
             # ephemeral stealth onion services are not supported
             self.supports_stealth = False
 
+    def is_authenticated(self):
+        """
+        Returns True if the Tor connection is still working, or False otherwise.
+        """
+        return self.c.is_authenticated()
+
     def start_onion_service(self, port):
         """
         Start a onion service on port 80, pointing to the given port, and
diff --git a/onionshare_gui/onionshare_gui.py b/onionshare_gui/onionshare_gui.py
index 3ed30db7..f6ebf6be 100644
--- a/onionshare_gui/onionshare_gui.py
+++ b/onionshare_gui/onionshare_gui.py
@@ -219,6 +219,11 @@ class OnionShareGui(QtWidgets.QMainWindow):
         def reload_settings():
             common.log('OnionShareGui', 'open_settings', 'settings have changed, reloading')
             self.settings.load()
+            # We might've stopped the main requests timer if a Tor connection failed.
+            # If we've reloaded settings, we probably succeeded in obtaining a new
+            # connection. If so, restart the timer.
+            if not self.timer.isActive():
+                self.timer.start()
 
         d = SettingsDialog(self.onion, self.qtapp, self.config)
         d.settings_saved.connect(reload_settings)
@@ -389,6 +394,18 @@ class OnionShareGui(QtWidgets.QMainWindow):
         """
         self.update()
 
+        # Have we lost connection to Tor somehow?
+        try:
+            # Tor Browser may not even have been open when we started OnionShare,
+            # in which case onion.is_authenticated() throws a NoneType error
+            self.onion
+            if not self.onion.is_authenticated():
+                self.timer.stop()
+                self.start_server_error(strings._('error_tor_protocol_error'))
+                self._tor_connection_canceled()
+        except:
+            pass
+
         # scroll to the bottom of the dl progress bar log pane
         # if a new download has been added
         if self.new_download:
diff --git a/onionshare_gui/settings_dialog.py b/onionshare_gui/settings_dialog.py
index df806a06..7ead3f1b 100644
--- a/onionshare_gui/settings_dialog.py
+++ b/onionshare_gui/settings_dialog.py
@@ -459,26 +459,31 @@ class SettingsDialog(QtWidgets.QDialog):
         # If Tor isn't connected, or if Tor settings have changed, Reinitialize
         # the Onion object
         reboot_onion = False
-        if self.onion.connected_to_tor:
-            def changed(s1, s2, keys):
-                """
-                Compare the Settings objects s1 and s2 and return true if any values
-                have changed for the given keys.
-                """
-                for key in keys:
-                    if s1.get(key) != s2.get(key):
-                        return True
-                return False
+        try:
+            self.onion
+            if self.onion.is_authenticated():
+                def changed(s1, s2, keys):
+                    """
+                    Compare the Settings objects s1 and s2 and return true if any values
+                    have changed for the given keys.
+                    """
+                    for key in keys:
+                        if s1.get(key) != s2.get(key):
+                            return True
+                    return False
 
-            if changed(settings, self.old_settings, [
-                'connection_type', 'control_port_address',
-                'control_port_port', 'socks_address', 'socks_port',
-                'socket_file_path', 'auth_type', 'auth_password']):
+                if changed(settings, self.old_settings, [
+                    'connection_type', 'control_port_address',
+                    'control_port_port', 'socks_address', 'socks_port',
+                    'socket_file_path', 'auth_type', 'auth_password']):
 
+                    reboot_onion = True
+
+            else:
+                # Tor isn't connected, so try connecting
                 reboot_onion = True
-
-        else:
-            # Tor isn't connected, so try connecting
+        except:
+            # We definitely aren't connected, as the onion object had no attribute is_authenticated()
             reboot_onion = True
 
         # Do we need to reinitialize Tor?