diff --git a/onionshare_gui/onionshare_gui.py b/onionshare_gui/onionshare_gui.py
index fd278394..8c354eeb 100644
--- a/onionshare_gui/onionshare_gui.py
+++ b/onionshare_gui/onionshare_gui.py
@@ -426,7 +426,6 @@ class OnionShareGui(QtWidgets.QMainWindow):
                     # close on finish?
                     if not web.get_stay_open():
                         self.server_status.stop_server()
-                        self.server_status.shutdown_timeout_reset()
                         self.status_bar.showMessage(strings._('closing_automatically', True))
                 else:
                     if self.server_status.status == self.server_status.STATUS_STOPPED:
@@ -449,7 +448,6 @@ class OnionShareGui(QtWidgets.QMainWindow):
                         if web.download_count == 0 or web.done:
                             self.server_status.stop_server()
                             self.status_bar.showMessage(strings._('close_on_timeout', True))
-                            self.server_status.shutdown_timeout_reset()
                         # A download is probably still running - hold off on stopping the share
                         else:
                             self.status_bar.showMessage(strings._('timeout_download_still_running', True))
diff --git a/onionshare_gui/server_status.py b/onionshare_gui/server_status.py
index 4e05bf22..48bffdca 100644
--- a/onionshare_gui/server_status.py
+++ b/onionshare_gui/server_status.py
@@ -119,6 +119,7 @@ class ServerStatus(QtWidgets.QVBoxLayout):
         """
         Reset the timeout in the UI after stopping a share
         """
+        self.server_shutdown_timeout_checkbox.setCheckState(QtCore.Qt.Unchecked)
         self.server_shutdown_timeout.setDateTime(QtCore.QDateTime.currentDateTime().addSecs(300))
         self.server_shutdown_timeout.setMinimumDateTime(QtCore.QDateTime.currentDateTime().addSecs(120))
 
@@ -196,7 +197,6 @@ class ServerStatus(QtWidgets.QVBoxLayout):
                 self.start_server()
         elif self.status == self.STATUS_STARTED:
             self.stop_server()
-            self.shutdown_timeout_reset()
 
     def start_server(self):
         """
@@ -219,6 +219,7 @@ class ServerStatus(QtWidgets.QVBoxLayout):
         Stop the server.
         """
         self.status = self.STATUS_WORKING
+        self.shutdown_timeout_reset()
         self.update()
         self.server_stopped.emit()