diff --git a/desktop/src/onionshare/connection_tab.py b/desktop/src/onionshare/connection_tab.py
index a8c8f8ec..096c503f 100644
--- a/desktop/src/onionshare/connection_tab.py
+++ b/desktop/src/onionshare/connection_tab.py
@@ -37,6 +37,7 @@ from .tor_connection import TorConnectionWidget
 from .update_checker import UpdateThread
 from .widgets import Alert
 
+
 class AutoConnectTab(QtWidgets.QWidget):
     """
     Initial Tab that appears in the very beginning to ask user if
@@ -81,7 +82,9 @@ class AutoConnectTab(QtWidgets.QWidget):
         self.image.setLayout(image_layout)
 
         # First launch widget
-        self.first_launch_widget = AutoConnectFirstLaunchWidget(self.common, self.curr_settings)
+        self.first_launch_widget = AutoConnectFirstLaunchWidget(
+            self.common, self.curr_settings
+        )
         self.first_launch_widget.toggle_auto_connect.connect(self.toggle_auto_connect)
         self.first_launch_widget.connect_clicked.connect(
             self.first_launch_widget_connect_clicked
@@ -168,7 +171,6 @@ class AutoConnectTab(QtWidgets.QWidget):
     def _got_no_bridges(self):
         self.use_bridge_widget.progress.hide()
         self.use_bridge_widget.progress_label.hide()
-        self.tor_con.fail.emit()
 
         Alert(
             self.common,
@@ -214,7 +216,10 @@ class AutoConnectTab(QtWidgets.QWidget):
                 self.common, self.common.gui.meek
             )
             self._censorship_progress_update(
-                75, strings._("gui_autoconnect_circumventing_censorship_requesting_bridges")
+                75,
+                strings._(
+                    "gui_autoconnect_circumventing_censorship_requesting_bridges"
+                ),
             )
             bridge_settings = self.censorship_circumvention.request_settings(
                 country=country
@@ -225,12 +230,14 @@ class AutoConnectTab(QtWidgets.QWidget):
                 self.curr_settings, bridge_settings
             ):
                 self._censorship_progress_update(
-                    100, strings._("gui_autoconnect_circumventing_censorship_got_bridges")
+                    100,
+                    strings._("gui_autoconnect_circumventing_censorship_got_bridges"),
                 )
                 self._got_bridges()
             else:
                 self._censorship_progress_update(
-                    100, strings._("gui_autoconnect_circumventing_censorship_no_bridges")
+                    100,
+                    strings._("gui_autoconnect_circumventing_censorship_no_bridges"),
                 )
                 self._got_no_bridges()
         except (
@@ -281,7 +288,7 @@ class AutoConnectTab(QtWidgets.QWidget):
             # Close the tab
             self.close_this_tab.emit()
 
-    def tor_con_fail(self):
+    def tor_con_fail(self, msg):
         """
         Finished testing tor connection.
         """
@@ -299,6 +306,9 @@ class AutoConnectTab(QtWidgets.QWidget):
         self.first_launch_widget.enable_autoconnect_checkbox.setChecked(
             self.auto_connect_enabled
         )
+        self.use_bridge_widget.hide()
+        self.first_launch_widget.show_buttons()
+        self.first_launch_widget.show()
 
 
 class AutoConnectFirstLaunchWidget(QtWidgets.QWidget):
@@ -323,9 +333,7 @@ class AutoConnectFirstLaunchWidget(QtWidgets.QWidget):
         self.enable_autoconnect_checkbox = ToggleCheckbox(
             strings._("gui_enable_autoconnect_checkbox")
         )
-        self.enable_autoconnect_checkbox.setChecked(
-            self.settings.get("auto_connect")
-        )
+        self.enable_autoconnect_checkbox.setChecked(self.settings.get("auto_connect"))
         self.enable_autoconnect_checkbox.clicked.connect(self._toggle_auto_connect)
         self.enable_autoconnect_checkbox.setFixedWidth(400)
         self.enable_autoconnect_checkbox.setStyleSheet(
diff --git a/desktop/src/onionshare/resources/locale/en.json b/desktop/src/onionshare/resources/locale/en.json
index 65a9c56d..d9ca9578 100644
--- a/desktop/src/onionshare/resources/locale/en.json
+++ b/desktop/src/onionshare/resources/locale/en.json
@@ -44,7 +44,7 @@
     "gui_tor_settings_window_title": "Tor Settings",
     "gui_autoconnect_description": "OnionShare relies on the Tor Network, run by thousands of volunteers around the world.",
     "gui_enable_autoconnect_checkbox": "Enable automatically connecting to Tor",
-    "gui_autoconnect_bridge_description": "<b>Failed connecting to Tor.</b> This could be because your internet is being censored. You might be able to bypass this censorship by using a bridge.",
+    "gui_autoconnect_bridge_description": "<b>Failed connecting to Tor.</b> This could be because your internet is being censored.<br>You might be able to bypass this censorship by using a bridge.<br><br>Or, you might just need to configure the Tor connection in Network Settings.",
     "gui_autoconnect_bridge_detect_automatic": "Automatically determine my country from my IP address, to bypass country-specific censorship",
     "gui_autoconnect_bridge_detect_manual": "Manually select my country instead",
     "gui_autoconnect_start": "Connect to Tor",
diff --git a/desktop/src/onionshare/tab_widget.py b/desktop/src/onionshare/tab_widget.py
index cacc658e..b810d607 100644
--- a/desktop/src/onionshare/tab_widget.py
+++ b/desktop/src/onionshare/tab_widget.py
@@ -255,7 +255,11 @@ class TabWidget(QtWidgets.QTabWidget):
                 return
 
         self.tor_settings_tab = TorSettingsTab(
-            self.common, self.current_tab_id, self.are_tabs_active(), self.status_bar, from_autoconnect
+            self.common,
+            self.current_tab_id,
+            self.are_tabs_active(),
+            self.status_bar,
+            from_autoconnect,
         )
         self.tor_settings_tab.close_this_tab.connect(self.close_tor_settings_tab)
         self.tor_settings_tab.tor_is_connected.connect(self.tor_is_connected)
@@ -385,10 +389,30 @@ class TabWidget(QtWidgets.QTabWidget):
 
     def close_tor_settings_tab(self):
         self.common.log("TabWidget", "close_tor_settings_tab")
-        for tab_id in self.tabs:
+        for tab_id in list(self.tabs):
             if type(self.tabs[tab_id]) is AutoConnectTab:
-                self.tabs[tab_id].reload_settings()
-        for tab_id in self.tabs:
+                # If we are being returned to the AutoConnectTab, but
+                # the user has fixed their Tor settings in the TorSettings
+                # tab, *and* they have enabled autoconnect, then
+                # we should close the AutoConnect Tab.
+                if self.common.gui.onion.is_authenticated():
+                    self.common.log(
+                        "TabWidget",
+                        "close_tor_settings_tab",
+                        "Tor is connected and we can auto-connect, so closing the tab",
+                    )
+                    index = self.indexOf(self.tabs[tab_id])
+                    self.close_tab(index)
+                else:
+                    self.tabs[tab_id].reload_settings()
+                    self.common.log(
+                        "TabWidget",
+                        "close_tor_settings_tab",
+                        "Reloading settings in case they changed in the TorSettingsTab. Not auto-connecting",
+                    )
+                break
+        # List of indices may have changed due to the above, so we loop over it again as another copy
+        for tab_id in list(self.tabs):
             if type(self.tabs[tab_id]) is TorSettingsTab:
                 index = self.indexOf(self.tabs[tab_id])
                 self.close_tab(index)
diff --git a/desktop/src/onionshare/tor_connection.py b/desktop/src/onionshare/tor_connection.py
index c69342ae..1f07242d 100644
--- a/desktop/src/onionshare/tor_connection.py
+++ b/desktop/src/onionshare/tor_connection.py
@@ -48,7 +48,7 @@ class TorConnectionWidget(QtWidgets.QWidget):
 
     open_tor_settings = QtCore.Signal()
     success = QtCore.Signal()
-    fail = QtCore.Signal()
+    fail = QtCore.Signal(str)
 
     def __init__(self, common, status_bar):
         super(TorConnectionWidget, self).__init__(None)
@@ -112,7 +112,7 @@ class TorConnectionWidget(QtWidgets.QWidget):
 
     def cancel_clicked(self):
         self.was_canceled = True
-        self.fail.emit()
+        self.fail.emit("")
 
     def wasCanceled(self):
         return self.was_canceled
@@ -141,17 +141,17 @@ class TorConnectionWidget(QtWidgets.QWidget):
         # Cancel connecting to Tor
         QtCore.QTimer.singleShot(1, self.cancel_clicked)
 
-    def _error_connecting_to_tor(self):
+    def _error_connecting_to_tor(self, msg):
         self.common.log("TorConnectionWidget", "_error_connecting_to_tor")
         self.active = False
-        self.fail.emit()
+        self.fail.emit(msg)
 
 
 class TorConnectionThread(QtCore.QThread):
     tor_status_update = QtCore.Signal(str, str)
     connected_to_tor = QtCore.Signal()
     canceled_connecting_to_tor = QtCore.Signal()
-    error_connecting_to_tor = QtCore.Signal()
+    error_connecting_to_tor = QtCore.Signal(str)
 
     def __init__(self, common, settings, parent):
         super(TorConnectionThread, self).__init__()
@@ -196,7 +196,7 @@ class TorConnectionThread(QtCore.QThread):
             self.common.log(
                 "TorConnectionThread", "run", f"caught exception: {message}"
             )
-            self.error_connecting_to_tor.emit()
+            self.error_connecting_to_tor.emit(message)
 
     def _tor_status_update(self, progress, summary):
         self.tor_status_update.emit(progress, summary)
diff --git a/desktop/src/onionshare/tor_settings_tab.py b/desktop/src/onionshare/tor_settings_tab.py
index 5ffea747..28cafc4c 100644
--- a/desktop/src/onionshare/tor_settings_tab.py
+++ b/desktop/src/onionshare/tor_settings_tab.py
@@ -691,7 +691,9 @@ class TorSettingsTab(QtWidgets.QWidget):
             # If Tor isn't connected, or if Tor settings have changed, Reinitialize
             # the Onion object
             reboot_onion = False
-            if not self.common.gui.local_only and not self.from_autoconnect:
+            if not self.common.gui.local_only and not (
+                self.from_autoconnect and not settings.get("auto_connect")
+            ):
                 if self.common.gui.onion.is_authenticated():
                     self.common.log(
                         "TorSettingsTab", "save_clicked", "Connected to Tor"