diff --git a/onionshare/onion.py b/onionshare/onion.py
index 2f4ddffd..b0499449 100644
--- a/onionshare/onion.py
+++ b/onionshare/onion.py
@@ -438,6 +438,10 @@ class Onion(object):
         return the onion hostname.
         """
         self.common.log('Onion', 'start_onion_service')
+        # Settings may have changed in the frontend but not updated in our settings object,
+        # such as persistence. Reload the settings now just to be sure.
+        self.settings.load()
+
         self.auth_string = None
 
         if not self.supports_ephemeral:
diff --git a/onionshare_gui/server_status.py b/onionshare_gui/server_status.py
index 3a6e31cc..dbcc6ca8 100644
--- a/onionshare_gui/server_status.py
+++ b/onionshare_gui/server_status.py
@@ -240,6 +240,9 @@ class ServerStatus(QtWidgets.QWidget):
         """
         # Set the URL fields
         if self.status == self.STATUS_STARTED:
+            # The backend Onion may have saved new settings, such as the private key.
+            # Reload the settings before saving new ones.
+            self.common.settings.load()
             self.show_url()
 
             if self.common.settings.get('save_private_key'):