diff --git a/src/main/java/org/cryptomator/ui/fxapp/UpdateChecker.java b/src/main/java/org/cryptomator/ui/fxapp/UpdateChecker.java
index a69384e41..0b593ef94 100644
--- a/src/main/java/org/cryptomator/ui/fxapp/UpdateChecker.java
+++ b/src/main/java/org/cryptomator/ui/fxapp/UpdateChecker.java
@@ -15,6 +15,7 @@ import javafx.beans.binding.BooleanBinding;
 import javafx.beans.binding.ObjectBinding;
 import javafx.beans.binding.StringExpression;
 import javafx.beans.property.ObjectProperty;
+import javafx.beans.property.SimpleObjectProperty;
 import javafx.concurrent.ScheduledService;
 import javafx.concurrent.Task;
 import javafx.util.Duration;
@@ -40,13 +41,14 @@ public class UpdateChecker extends ScheduledService<UpdateInfo<?>> {
 	private final Environment env;
 	private final Settings settings;
 	private final ObjectProperty<Instant> lastSuccessfulUpdateCheck;
-	private final StringExpression latestVersion = StringExpression.stringExpression(lastValueProperty().map(UpdateInfo::version));
-	private final BooleanBinding updateAvailable = lastValueProperty().isNotNull();
+	private final ObjectProperty<UpdateInfo<?>> update = new SimpleObjectProperty<>();
+	private final StringExpression latestVersion = StringExpression.stringExpression(update.map(UpdateInfo::version));
+	private final BooleanBinding updateAvailable = update.isNotNull();
 	private final ObjectBinding<UpdateCheckState> updateState = Bindings.createObjectBinding(this::getUpdateCheckState, stateProperty());
 	private final BooleanBinding checkFailed = Bindings.equal(UpdateCheckState.CHECK_FAILED, updateState);
 	private final HttpClient httpClient;
-	private final UpdateMechanism<?> primaryUpdateMechanism;
 	private final UpdateMechanism<?> fallbackUpdateMechanism;
+	private UpdateMechanism<?> updateMechanism;
 
 	@Inject
 	UpdateChecker(Settings settings, //
@@ -63,9 +65,9 @@ public class UpdateChecker extends ScheduledService<UpdateInfo<?>> {
 		var currentVersion = env.getAppVersionWithBuildNumber();
 		var lastAttemptedBy = settings.lastUpdateAttemptedByVersion.get();
 		if (currentVersion != null && currentVersion.equals(lastAttemptedBy)) {
-			this.primaryUpdateMechanism = fallbackUpdateMechanism; // immediately use fallback mechanism
+			this.updateMechanism = fallbackUpdateMechanism; // immediately use fallback mechanism
 		} else {
-			this.primaryUpdateMechanism = UpdateMechanism.get().orElse(fallbackUpdateMechanism);
+			this.updateMechanism = UpdateMechanism.get().orElse(fallbackUpdateMechanism);
 		}
 
 		setExecutor(Executors.newVirtualThreadPerTaskExecutor());
@@ -78,6 +80,14 @@ public class UpdateChecker extends ScheduledService<UpdateInfo<?>> {
 		}
 	}
 
+	public void recheckWithFallbackMechanism() {
+		if (updateMechanism == fallbackUpdateMechanism) {
+			return; // already using fallback mechanism
+		}
+		updateMechanism = fallbackUpdateMechanism;
+		checkForUpdatesNow();
+	}
+
 	public void checkForUpdatesNow() {
 		startCheckingForUpdates(Duration.ZERO);
 	}
@@ -96,6 +106,7 @@ public class UpdateChecker extends ScheduledService<UpdateInfo<?>> {
 		lastSuccessfulUpdateCheck.set(Instant.now());
 		if (updateInfo != null) {
 			LOG.info("Current version: {}, latest version: {}", getCurrentVersion(), updateInfo.version());
+			update.set(updateInfo);
 		}
 	}
 
@@ -106,6 +117,14 @@ public class UpdateChecker extends ScheduledService<UpdateInfo<?>> {
 
 	/* Observable Properties */
 
+	public UpdateInfo<?> getUpdate() {
+		return update.get();
+	}
+
+	public ObjectProperty<UpdateInfo<?>> updateProperty() {
+		return update;
+	}
+
 	public String getLatestVersion() {
 		return latestVersion.get();
 	}
@@ -160,14 +179,14 @@ public class UpdateChecker extends ScheduledService<UpdateInfo<?>> {
 		@Override
 		protected UpdateInfo<?> call() {
 			try {
-				var result = primaryUpdateMechanism.checkForUpdate(env.getAppVersion(), httpClient);
+				var result = updateMechanism.checkForUpdate(env.getAppVersion(), httpClient);
 				if (result != null) {
 					return result;
 				}
 			} catch (UpdateFailedException e) {
-				LOG.error("Primary update check failed.", e);
+				LOG.error("Update check using {} failed.", updateMechanism.getClass(), e);
 			}
-			if (primaryUpdateMechanism == fallbackUpdateMechanism) {
+			if (updateMechanism == fallbackUpdateMechanism) {
 				return null;
 			}
 			LOG.debug("Trying fallback update check...");
diff --git a/src/main/java/org/cryptomator/ui/preferences/UpdatesPreferencesController.java b/src/main/java/org/cryptomator/ui/preferences/UpdatesPreferencesController.java
index 129abff3a..072b46f8c 100644
--- a/src/main/java/org/cryptomator/ui/preferences/UpdatesPreferencesController.java
+++ b/src/main/java/org/cryptomator/ui/preferences/UpdatesPreferencesController.java
@@ -75,7 +75,7 @@ public class UpdatesPreferencesController implements FxController {
 		this.resourceBundle = resourceBundle;
 		this.settings = settings;
 		this.updateChecker = updateChecker;
-		this.updateService = new UpdateService(updateChecker.lastValueProperty());
+		this.updateService = new UpdateService(updateChecker.updateProperty());
 		this.vaultService = vaultService;
 		this.worker = Bindings.when(updateChecker.updateAvailableProperty()).<Worker<?>>then(this.updateService).otherwise(this.updateChecker);
 		this.running = Bindings.createBooleanBinding(this::isRunning, updateService.stateProperty(), updateChecker.stateProperty());
@@ -84,7 +84,7 @@ public class UpdatesPreferencesController implements FxController {
 		this.timeDifferenceMessage = Bindings.createStringBinding(this::getTimeDifferenceMessage, updateChecker.lastSuccessfulUpdateCheckProperty());
 		this.lastUpdateCheckMessage = Bindings.createStringBinding(this::getLastUpdateCheckMessage, updateChecker.lastSuccessfulUpdateCheckProperty());
 		this.unlockedVaults = vaults.filtered(Vault::isUnlocked);
-		this.prohibitUpdateWhileUnlocked = Bindings.createBooleanBinding(this::isProhibitUpdateWhileUnlocked, unlockedVaults, updateChecker.lastValueProperty());
+		this.prohibitUpdateWhileUnlocked = Bindings.createBooleanBinding(this::isProhibitUpdateWhileUnlocked, unlockedVaults, updateChecker.updateProperty());
 		this.updateButtonDisabled = Bindings.when(worker.isEqualTo(updateChecker)).then(running).otherwise(prohibitUpdateWhileUnlocked.or(running));
 	}
 
@@ -114,7 +114,7 @@ public class UpdatesPreferencesController implements FxController {
 		} else if (!unlockedVaults.isEmpty()) {
 			LOG.warn("Cannot start update due to unlocked vaults.");
 		} else if (worker.get().equals(updateService)) {
-			LOG.info("User started update to version {}", updateChecker.getLastValue().version());
+			LOG.info("User started update to version {}", updateChecker.getUpdate().version());
 			updateService.start();
 		}
 	}
@@ -138,7 +138,8 @@ public class UpdatesPreferencesController implements FxController {
 	private void updateFailed(WorkerStateEvent workerStateEvent) {
 		assert workerStateEvent.getSource() == updateService;
 		LOG.error("Update failed.", updateService.getException());
-		// TODO: show error to user? use fallback update service?
+		// try fallback mechanism:
+		updateChecker.recheckWithFallbackMechanism();
 		updateService.reset();
 	}
 
@@ -178,7 +179,7 @@ public class UpdatesPreferencesController implements FxController {
 			return resourceBundle.getString("preferences.updates.checkNowBtn");
 		} else {
 			return switch (updateService.getState()) {
-				case READY -> updateChecker.getLastValue().updateMechanism().getName();
+				case READY -> updateChecker.getUpdate().updateMechanism().getName();
 				case SCHEDULED, RUNNING -> updateService.getMessage(); // "Preparing Update..."; // TODO: resourceBundle.getString("preferences.updates.preparingUpdate")...
 				case SUCCEEDED -> "Restart to Update"; // TODO: resourceBundle.getString("preferences.updates.readyToRestart")...
 				case FAILED, CANCELLED -> "failed";
@@ -234,7 +235,7 @@ public class UpdatesPreferencesController implements FxController {
 
 	public boolean isProhibitUpdateWhileUnlocked() {
 		// If the result of the last update check was from the fallback mechanism, we don't need to show the warning
-		return !unlockedVaults.isEmpty() && !FallbackUpdateInfo.class.isInstance(updateChecker.getLastValue());
+		return !unlockedVaults.isEmpty() && !FallbackUpdateInfo.class.isInstance(updateChecker.getUpdate());
 	}
 
 	public BooleanBinding prohibitUpdateWhileUnlockedProperty() {