diff --git a/onionshare/onion.py b/onionshare/onion.py
index 05909a40..1e8d45e3 100644
--- a/onionshare/onion.py
+++ b/onionshare/onion.py
@@ -139,6 +139,9 @@ class Onion(object):
         # The tor process
         self.tor_proc = None
 
+        # Start out not connected to Tor
+        self.connected_to_tor = False
+
     def connect(self, settings=False, tor_status_update_func=None):
         common.log('Onion', 'connect')
 
@@ -332,6 +335,9 @@ class Onion(object):
             except AuthenticationFailure:
                 raise TorErrorAuthError(strings._('settings_error_auth').format(self.settings.get('control_port_address'), self.settings.get('control_port_port')))
 
+        # If we made it this far, we should be connected to Tor
+        self.connected_to_tor = True
+
         # Get the tor version
         self.tor_version = self.c.get_version().version_str
 
diff --git a/onionshare_gui/onionshare_gui.py b/onionshare_gui/onionshare_gui.py
index 91ccc9ec..76811ccb 100644
--- a/onionshare_gui/onionshare_gui.py
+++ b/onionshare_gui/onionshare_gui.py
@@ -61,7 +61,7 @@ class OnionShareGui(QtWidgets.QMainWindow):
         self.settings.load()
 
         # Start the "Connecting to Tor" dialog, which calls onion.connect()
-        tor_con = TorConnectionDialog(self.settings, self.onion)
+        tor_con = TorConnectionDialog(self.qtapp, self.settings, self.onion)
         tor_con.canceled.connect(self._tor_connection_canceled)
         tor_con.open_settings.connect(self._tor_connection_open_settings)
         tor_con.start()
diff --git a/onionshare_gui/tor_connection_dialog.py b/onionshare_gui/tor_connection_dialog.py
index 5e072e8e..c0efd172 100644
--- a/onionshare_gui/tor_connection_dialog.py
+++ b/onionshare_gui/tor_connection_dialog.py
@@ -30,10 +30,11 @@ class TorConnectionDialog(QtWidgets.QProgressDialog):
     """
     open_settings = QtCore.pyqtSignal()
 
-    def __init__(self, settings, onion):
+    def __init__(self, qtapp, settings, onion):
         super(TorConnectionDialog, self).__init__(None)
         common.log('TorConnectionDialog', '__init__')
 
+        self.qtapp = qtapp
         self.settings = settings
         self.onion = onion
 
@@ -51,45 +52,53 @@ class TorConnectionDialog(QtWidgets.QProgressDialog):
         self.setMinimumDuration(100)
 
         # Start displaying the status at 0
-        self.tor_status_update(0, '')
+        self._tor_status_update(0, '')
 
     def start(self):
         common.log('TorConnectionDialog', 'start')
 
         t = TorConnectionThread(self, self.settings, self.onion)
-        t.tor_status_update.connect(self.tor_status_update)
-        t.connected_to_tor.connect(self.connected_to_tor)
-        t.canceled_connecting_to_tor.connect(self.canceled_connecting_to_tor)
-        t.error_connecting_to_tor.connect(self.error_connecting_to_tor)
+        t.tor_status_update.connect(self._tor_status_update)
+        t.connected_to_tor.connect(self._connected_to_tor)
+        t.canceled_connecting_to_tor.connect(self._canceled_connecting_to_tor)
+        t.error_connecting_to_tor.connect(self._error_connecting_to_tor)
         t.start()
 
-        # Wait for the thread to start
-        time.sleep(0.1)
+        # The main thread needs to remain active, and checkign for Qt events,
+        # until the thread is finished. Otherwise it won't be able to handle
+        # accepting signals.
+        self.active = True
+        while self.active:
+            time.sleep(0.1)
+            self.qtapp.processEvents()
 
-    def tor_status_update(self, progress, summary):
+    def _tor_status_update(self, progress, summary):
         self.setValue(int(progress))
         self.setLabelText("<strong>{}</strong><br>{}".format(strings._('connecting_to_tor', True), summary))
 
-    def connected_to_tor(self):
-        common.log('TorConnectionDialog', 'connected_to_tor')
+    def _connected_to_tor(self):
+        common.log('TorConnectionDialog', '_connected_to_tor')
+        self.active = False
 
         # Close the dialog after connecting
         self.setValue(self.maximum())
 
-    def canceled_connecting_to_tor(self):
-        common.log('TorConnectionDialog', 'canceled_connecting_to_tor')
+    def _canceled_connecting_to_tor(self):
+        common.log('TorConnectionDialog', '_canceled_connecting_to_tor')
+        self.active = False
 
         # Cancel connecting to Tor
         self.cancel()
 
-    def error_connecting_to_tor(self):
-        common.log('TorConnectionDialog', 'error_connecting_to_tor')
+    def _error_connecting_to_tor(self, msg):
+        common.log('TorConnectionDialog', '_error_connecting_to_tor')
+        self.active = False
 
         # Cancel connecting to Tor
         self.cancel()
 
         # Display the exception in an alert box
-        Alert("{}\n\n{}".format(e.args[0], strings._('gui_tor_connection_error_settings', True)), QtWidgets.QMessageBox.Warning)
+        Alert("{}\n\n{}".format(msg, strings._('gui_tor_connection_error_settings', True)), QtWidgets.QMessageBox.Warning)
 
         # Open settings
         self.open_settings.emit()
@@ -113,15 +122,18 @@ class TorConnectionThread(QtCore.QThread):
 
         # Connect to the Onion
         try:
-            common.log('TorConnectionThread', 'run', 'about to run onion.connect')
             self.onion.connect(self.settings, self._tor_status_update)
-            common.log('TorConnectionThread', 'run', 'onion.connect succeeded')
-            self.connected_to_tor.emit()
+            if self.onion.connected_to_tor:
+                self.connected_to_tor.emit()
+            else:
+                self.error_connecting_to_tor.emit(strings._('settings_error_unknown_error', True))
 
         except BundledTorCanceled as e:
-            self.canceled_connecting_to_tor.emit()
+            common.log('TorConnectionThread', 'run', 'caught exception: BundledTorCanceled')
+            self.canceled_connecting_to_tor.emit(strings._('settings_error_bundled_tor_canceled'))
 
         except Exception as e:
+            common.log('TorConnectionThread', 'run', 'caught exception: {}'.format(e.args[0]))
             self.error_connecting_to_tor.emit(e.args[0])
 
     def _tor_status_update(self, progress, summary):
diff --git a/share/locale/en.json b/share/locale/en.json
index cd346868..3cf17548 100644
--- a/share/locale/en.json
+++ b/share/locale/en.json
@@ -91,8 +91,10 @@
     "settings_error_auth": "Connected to {}:{}, but can't authenticate. Maybe this isn't a Tor controller?",
     "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_error_bundled_tor_not_supported": "Bundled Tor is not supported when not using developer mode in Windows or macOS.",
+    "settings_error_bundled_tor_timeout": "Connecting to Tor is taking too long. Maybe your computer is offline, or your clock isn't accurate.",
+    "settings_error_bundled_tor_canceled": "The Tor process closed before it could finish connecting.",
+    "settings_error_unknown_error": "Failed connecting to Tor for an unknown reasons.",
     "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",