diff --git a/src/vs/workbench/contrib/update/browser/update.ts b/src/vs/workbench/contrib/update/browser/update.ts
index 2138c3827ba..1547ad559f3 100644
--- a/src/vs/workbench/contrib/update/browser/update.ts
+++ b/src/vs/workbench/contrib/update/browser/update.ts
@@ -529,53 +529,58 @@ export class SwitchProductQualityContribution extends Disposable implements IWor
 					const storageService = accessor.get(IStorageService);
 					const userDataSyncWorkbenchService = accessor.get(IUserDataSyncWorkbenchService);
 					const userDataSyncService = accessor.get(IUserDataSyncService);
+					const notificationService = accessor.get(INotificationService);
 
-					const selectSettingsSyncServiceDialogShownKey = 'switchQuality.selectSettingsSyncServiceDialogShown';
-					const userDataSyncStore = userDataSyncStoreManagementService.userDataSyncStore;
-					let userDataSyncStoreType: UserDataSyncStoreType | undefined;
-					if (userDataSyncStore && isSwitchingToInsiders && userDataAutoSyncEnablementService.isEnabled()
-						&& !storageService.getBoolean(selectSettingsSyncServiceDialogShownKey, StorageScope.GLOBAL, false)) {
-						userDataSyncStoreType = await this.selectSettingsSyncService(dialogService);
-						if (!userDataSyncStoreType) {
-							return;
-						}
-						storageService.store(selectSettingsSyncServiceDialogShownKey, true, StorageScope.GLOBAL, StorageTarget.USER);
-						if (userDataSyncStoreType === 'stable') {
-							// Update the stable service type in the current window, so that it uses stable service after switched to insiders version (after reload).
-							await userDataSyncStoreManagementService.switch(userDataSyncStoreType);
-						}
-					}
-
-					const res = await dialogService.confirm({
-						type: 'info',
-						message: nls.localize('relaunchMessage', "Changing the version requires a reload to take effect"),
-						detail: newQuality === 'insider' ?
-							nls.localize('relaunchDetailInsiders', "Press the reload button to switch to the nightly pre-production version of VSCode.") :
-							nls.localize('relaunchDetailStable', "Press the reload button to switch to the monthly released stable version of VSCode."),
-						primaryButton: nls.localize('reload', "&&Reload")
-					});
-
-					if (res.confirmed) {
-						const promises: Promise<any>[] = [];
-
-						// If sync is happening wait until it is finished before reload
-						if (userDataSyncService.status === SyncStatus.Syncing) {
-							promises.push(Event.toPromise(Event.filter(userDataSyncService.onDidChangeStatus, status => status !== SyncStatus.Syncing)));
+					try {
+						const selectSettingsSyncServiceDialogShownKey = 'switchQuality.selectSettingsSyncServiceDialogShown';
+						const userDataSyncStore = userDataSyncStoreManagementService.userDataSyncStore;
+						let userDataSyncStoreType: UserDataSyncStoreType | undefined;
+						if (userDataSyncStore && isSwitchingToInsiders && userDataAutoSyncEnablementService.isEnabled()
+							&& !storageService.getBoolean(selectSettingsSyncServiceDialogShownKey, StorageScope.GLOBAL, false)) {
+							userDataSyncStoreType = await this.selectSettingsSyncService(dialogService);
+							if (!userDataSyncStoreType) {
+								return;
+							}
+							storageService.store(selectSettingsSyncServiceDialogShownKey, true, StorageScope.GLOBAL, StorageTarget.USER);
+							if (userDataSyncStoreType === 'stable') {
+								// Update the stable service type in the current window, so that it uses stable service after switched to insiders version (after reload).
+								await userDataSyncStoreManagementService.switch(userDataSyncStoreType);
+							}
 						}
 
-						// Synchronise the store type option in insiders service, so that other clients using insiders service are also updated.
-						if (isSwitchingToInsiders) {
-							promises.push(userDataSyncWorkbenchService.synchroniseUserDataSyncStoreType());
-						}
+						const res = await dialogService.confirm({
+							type: 'info',
+							message: nls.localize('relaunchMessage', "Changing the version requires a reload to take effect"),
+							detail: newQuality === 'insider' ?
+								nls.localize('relaunchDetailInsiders', "Press the reload button to switch to the nightly pre-production version of VSCode.") :
+								nls.localize('relaunchDetailStable', "Press the reload button to switch to the monthly released stable version of VSCode."),
+							primaryButton: nls.localize('reload', "&&Reload")
+						});
 
-						await Promises.settled(promises);
+						if (res.confirmed) {
+							const promises: Promise<any>[] = [];
 
-						productQualityChangeHandler(newQuality);
-					} else {
-						// Reset
-						if (userDataSyncStoreType) {
-							storageService.remove(selectSettingsSyncServiceDialogShownKey, StorageScope.GLOBAL);
+							// If sync is happening wait until it is finished before reload
+							if (userDataSyncService.status === SyncStatus.Syncing) {
+								promises.push(Event.toPromise(Event.filter(userDataSyncService.onDidChangeStatus, status => status !== SyncStatus.Syncing)));
+							}
+
+							// If user chose the sync service then synchronise the store type option in insiders service, so that other clients using insiders service are also updated.
+							if (isSwitchingToInsiders && userDataSyncStoreType) {
+								promises.push(userDataSyncWorkbenchService.synchroniseUserDataSyncStoreType());
+							}
+
+							await Promises.settled(promises);
+
+							productQualityChangeHandler(newQuality);
+						} else {
+							// Reset
+							if (userDataSyncStoreType) {
+								storageService.remove(selectSettingsSyncServiceDialogShownKey, StorageScope.GLOBAL);
+							}
 						}
+					} catch (error) {
+						notificationService.error(error);
 					}
 				}