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src/main/java/org/cryptomator/ui/preferences/UpdatesPreferencesController.java

@@ -119,6 +119,7 @@ public class UpdatesPreferencesController implements FxController {
 	private void updateFailed(WorkerStateEvent workerStateEvent) {
 		assert workerStateEvent.getSource() == updateService;
 		LOG.error("Update failed.", updateService.getException());
+		updateService.reset();
 	}
 
 	/* Observable Properties */

src/main/java/org/cryptomator/updater/FallbackUpdateMechanism.java

@@ -66,7 +66,11 @@ public class FallbackUpdateMechanism implements UpdateMechanism<UpdateInfo> {
 			} else {
 				return null;
 			}
-		} catch (IOException | InterruptedException e) {
+		} catch (InterruptedException e) {
+			Thread.currentThread().interrupt();
+			LOG.warn("Update check interrupted", e);
+			return null;
+		} catch (IOException e) {
 			LOG.warn("Update check failed", e);
 			return null;
 		}

src/main/java/org/cryptomator/updater/MacOsDmgUpdateMechanism.java

@@ -96,6 +96,7 @@ public class MacOsDmgUpdateMechanism extends DownloadUpdateMechanism {
 				}
 				LOG.debug("Update ready: {}", workDir.resolve("Cryptomator.app"));
 			} catch (InterruptedException e) {
+				Thread.currentThread().interrupt();
 				throw new InterruptedIOException("Failed to extract DMG, interrupted");
 			}
 			return UpdateStep.of("Restarting...", this::restart);