diff --git a/securedrop_client/logic.py b/securedrop_client/logic.py
index aa9298f402..3afc2aa32b 100644
--- a/securedrop_client/logic.py
+++ b/securedrop_client/logic.py
@@ -321,7 +321,8 @@ def call_api(self,
         new_api_thread.start()
 
     def on_queue_paused(self) -> None:
-        self.gui.update_error_status(_('The SecureDrop server cannot be reached.'), duration=0)
+        self.gui.update_error_status(
+            _('The SecureDrop server cannot be reached. Trying to reconnect...'), duration=0)
         self.show_last_sync_timer.start(TIME_BETWEEN_SHOWING_LAST_SYNC_MS)
 
     def resume_queues(self) -> None:
@@ -461,6 +462,9 @@ def on_sync_failure(self, result: Exception) -> None:
             self.invalidate_token()
             self.logout()
             self.gui.show_login(error=_('Your session expired. Please log in again.'))
+        elif isinstance(result, (RequestTimeoutError, ServerConnectionError)):
+            self.gui.update_error_status(
+                _('The SecureDrop server cannot be reached. Trying to reconnect...'), duration=0)
 
     def show_last_sync(self):
         """
diff --git a/tests/test_logic.py b/tests/test_logic.py
index c452834e24..187f016bcc 100644
--- a/tests/test_logic.py
+++ b/tests/test_logic.py
@@ -427,6 +427,38 @@ def test_Controller_on_sync_failure_due_to_invalid_token(homedir, config, mocker
     co.gui.show_login.assert_called_once_with(error='Your session expired. Please log in again.')
 
 
+def test_Controller_on_sync_failure_due_to_request_timeout(homedir, config, mocker, session_maker):
+    """
+    If the sync fails because of a request timeout, make sure to show an error message.
+    """
+    gui = mocker.MagicMock()
+    co = Controller('http://localhost', gui, session_maker, homedir)
+    co.logout = mocker.MagicMock()
+    co.gui = mocker.MagicMock()
+    co.gui.update_error_status = mocker.MagicMock()
+
+    co.on_sync_failure(RequestTimeoutError())
+
+    co.gui.update_error_status.assert_called_once_with(
+        'The SecureDrop server cannot be reached. Trying to reconnect...', duration=0)
+
+
+def test_Controller_on_sync_failure_due_to_connect_timeout(homedir, config, mocker, session_maker):
+    """
+    If the sync fails because of a connect timeout, make sure to show an error message.
+    """
+    gui = mocker.MagicMock()
+    co = Controller('http://localhost', gui, session_maker, homedir)
+    co.logout = mocker.MagicMock()
+    co.gui = mocker.MagicMock()
+    co.gui.update_error_status = mocker.MagicMock()
+
+    co.on_sync_failure(ServerConnectionError())
+
+    co.gui.update_error_status.assert_called_once_with(
+        'The SecureDrop server cannot be reached. Trying to reconnect...', duration=0)
+
+
 def test_Controller_on_sync_success(homedir, config, mocker):
     """
     If there's a result to syncing, then update local storage.
@@ -1489,7 +1521,7 @@ def test_Controller_on_queue_paused(homedir, config, mocker, session_maker):
     co.show_last_sync_timer = mocker.MagicMock()
     co.on_queue_paused()
     mock_gui.update_error_status.assert_called_once_with(
-        'The SecureDrop server cannot be reached.', duration=0)
+        'The SecureDrop server cannot be reached. Trying to reconnect...', duration=0)
     co.show_last_sync_timer.start.assert_called_once_with(TIME_BETWEEN_SHOWING_LAST_SYNC_MS)