diff --git a/synodic_client/application/update_controller.py b/synodic_client/application/update_controller.py
index 0204841..e1cf84a 100644
--- a/synodic_client/application/update_controller.py
+++ b/synodic_client/application/update_controller.py
@@ -440,8 +440,8 @@ def _apply_update(self, *, silent: bool = False) -> None:
             # the next launch.
             sync_startup(sys.executable, auto_start=self._store.config.auto_start)
 
-            self._pending_version = None
             self._client.apply_update_on_exit(restart=True, silent=silent)
+            self._pending_version = None
             logger.info('Update scheduled — restarting application')
             self._app.quit()
         except Exception as e:
diff --git a/synodic_client/updater.py b/synodic_client/updater.py
index 61761d3..34c8d2a 100644
--- a/synodic_client/updater.py
+++ b/synodic_client/updater.py
@@ -184,7 +184,12 @@ def check_for_update(self) -> UpdateInfo:
                     latest_version=latest,
                     _velopack_info=velopack_info,
                 )
-                self._state = UpdateState.UPDATE_AVAILABLE
+                # Only advance to UPDATE_AVAILABLE if we haven't already
+                # moved past it.  A periodic re-check that discovers the
+                # same release must not regress DOWNLOADED → UPDATE_AVAILABLE,
+                # which would cause apply_update_on_exit() to reject the update.
+                if self._state not in (UpdateState.DOWNLOADED, UpdateState.APPLYING, UpdateState.APPLIED):
+                    self._state = UpdateState.UPDATE_AVAILABLE
                 logger.info('Update available: %s -> %s', self._current_version, latest)
             else:
                 self._update_info = UpdateInfo(
diff --git a/tests/unit/test_updater.py b/tests/unit/test_updater.py
index 887a0cb..ac932c2 100644
--- a/tests/unit/test_updater.py
+++ b/tests/unit/test_updater.py
@@ -227,6 +227,38 @@ def test_check_non_404_http_error_is_failed(updater: Updater) -> None:
         assert info.available is False
         assert updater.state == UpdateState.FAILED
 
+    @staticmethod
+    def test_check_preserves_downloaded_state(updater: Updater) -> None:
+        """Re-checking after download must not regress DOWNLOADED → UPDATE_AVAILABLE.
+
+        Regression test: when the periodic auto-check timer fires between
+        download completion and the user clicking "Restart Now", the state
+        was incorrectly reset to UPDATE_AVAILABLE, causing apply_update_on_exit
+        to reject the update with "No downloaded update to apply".
+        """
+        mock_target = MagicMock(spec=velopack.VelopackAsset)
+        mock_target.Version = '2.0.0'
+        mock_velopack_info = MagicMock(spec=velopack.UpdateInfo)
+        mock_velopack_info.TargetFullRelease = mock_target
+
+        mock_manager = MagicMock(spec=velopack.UpdateManager)
+        mock_manager.check_for_updates.return_value = mock_velopack_info
+
+        # Simulate: download already completed
+        updater._state = UpdateState.DOWNLOADED
+        updater._update_info = UpdateInfo(
+            available=True,
+            current_version=Version('1.0.0'),
+            latest_version=Version('2.0.0'),
+            _velopack_info=mock_velopack_info,
+        )
+
+        with patch.object(updater, '_get_velopack_manager', return_value=mock_manager):
+            info = updater.check_for_update()
+
+        assert info.available is True
+        assert updater.state == UpdateState.DOWNLOADED
+
 
 class TestUpdaterDownloadUpdate:
     """Tests for download_update method."""