diff --git a/src/vs/platform/userDataSync/common/userDataSync.ts b/src/vs/platform/userDataSync/common/userDataSync.ts
index a79be906630..e4c71928b42 100644
--- a/src/vs/platform/userDataSync/common/userDataSync.ts
+++ b/src/vs/platform/userDataSync/common/userDataSync.ts
@@ -357,6 +357,7 @@ export interface IUserDataSyncService {
 
 	readonly status: SyncStatus;
 	readonly onDidChangeStatus: Event<SyncStatus>;
+	readonly onSynchronizeResource: Event<SyncResource>;
 
 	readonly conflicts: SyncResourceConflicts[];
 	readonly onDidChangeConflicts: Event<SyncResourceConflicts[]>;
diff --git a/src/vs/platform/userDataSync/common/userDataSyncIpc.ts b/src/vs/platform/userDataSync/common/userDataSyncIpc.ts
index 2df27100016..467f6902fe6 100644
--- a/src/vs/platform/userDataSync/common/userDataSyncIpc.ts
+++ b/src/vs/platform/userDataSync/common/userDataSyncIpc.ts
@@ -22,6 +22,7 @@ export class UserDataSyncChannel implements IServerChannel {
 	listen(_: unknown, event: string): Event<any> {
 		switch (event) {
 			case 'onDidChangeStatus': return this.service.onDidChangeStatus;
+			case 'onSynchronizeResource': return this.service.onSynchronizeResource;
 			case 'onDidChangeConflicts': return this.service.onDidChangeConflicts;
 			case 'onDidChangeLocal': return this.service.onDidChangeLocal;
 			case 'onDidChangeLastSyncTime': return this.service.onDidChangeLastSyncTime;
diff --git a/src/vs/platform/userDataSync/common/userDataSyncService.ts b/src/vs/platform/userDataSync/common/userDataSyncService.ts
index a1e9c9592c9..2fadc715911 100644
--- a/src/vs/platform/userDataSync/common/userDataSyncService.ts
+++ b/src/vs/platform/userDataSync/common/userDataSyncService.ts
@@ -39,6 +39,9 @@ export class UserDataSyncService extends Disposable implements IUserDataSyncServ
 	private _onDidChangeStatus: Emitter<SyncStatus> = this._register(new Emitter<SyncStatus>());
 	readonly onDidChangeStatus: Event<SyncStatus> = this._onDidChangeStatus.event;
 
+	private _onSynchronizeResource: Emitter<SyncResource> = this._register(new Emitter<SyncResource>());
+	readonly onSynchronizeResource: Event<SyncResource> = this._onSynchronizeResource.event;
+
 	readonly onDidChangeLocal: Event<SyncResource>;
 
 	private _conflicts: SyncResourceConflicts[] = [];
@@ -91,6 +94,7 @@ export class UserDataSyncService extends Disposable implements IUserDataSyncServ
 		try {
 			for (const synchroniser of this.synchronisers) {
 				try {
+					this._onSynchronizeResource.fire(synchroniser.resource);
 					await synchroniser.pull();
 				} catch (e) {
 					this.handleSynchronizerError(e, synchroniser.resource);
@@ -175,6 +179,7 @@ export class UserDataSyncService extends Disposable implements IUserDataSyncServ
 					return;
 				}
 				try {
+					this._onSynchronizeResource.fire(synchroniser.resource);
 					await synchroniser.sync(manifest, syncHeaders);
 				} catch (e) {
 					this.handleSynchronizerError(e, synchroniser.resource);
diff --git a/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts b/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts
index a2b39520076..39cf3d651fa 100644
--- a/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts
+++ b/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts
@@ -6,7 +6,7 @@
 import { IUserDataSyncService, IAuthenticationProvider, getUserDataSyncStore, isAuthenticationProvider, IUserDataAutoSyncService } from 'vs/platform/userDataSync/common/userDataSync';
 import { ITelemetryService } from 'vs/platform/telemetry/common/telemetry';
 import { registerSingleton } from 'vs/platform/instantiation/common/extensions';
-import { IUserDataSyncWorkbenchService, IUserDataSyncAccount, AccountStatus, CONTEXT_SYNC_ENABLEMENT, CONTEXT_SYNC_STATE, CONTEXT_ACCOUNT_STATE, SHOW_SYNCED_DATA_COMMAND_ID } from 'vs/workbench/services/userDataSync/common/userDataSync';
+import { IUserDataSyncWorkbenchService, IUserDataSyncAccount, AccountStatus, CONTEXT_SYNC_ENABLEMENT, CONTEXT_SYNC_STATE, CONTEXT_ACCOUNT_STATE, SHOW_SYNCED_DATA_COMMAND_ID, SHOW_SYNC_LOG_COMMAND_ID, getSyncAreaLabel } from 'vs/workbench/services/userDataSync/common/userDataSync';
 import { AuthenticationSession, AuthenticationSessionsChangeEvent } from 'vs/editor/common/modes';
 import { Disposable, DisposableStore } from 'vs/base/common/lifecycle';
 import { Emitter, Event } from 'vs/base/common/event';
@@ -28,6 +28,7 @@ import { IDialogService } from 'vs/platform/dialogs/common/dialogs';
 import { IContextKey, IContextKeyService } from 'vs/platform/contextkey/common/contextkey';
 import { ICommandService } from 'vs/platform/commands/common/commands';
 import { Action } from 'vs/base/common/actions';
+import { IProgressService, ProgressLocation } from 'vs/platform/progress/common/progress';
 
 type UserAccountClassification = {
 	id: { classification: 'EndUserPseudonymizedInformation', purpose: 'BusinessInsight' };
@@ -90,6 +91,7 @@ export class UserDataSyncWorkbenchService extends Disposable implements IUserDat
 		@IExtensionService extensionService: IExtensionService,
 		@IWorkbenchEnvironmentService private readonly environmentService: IWorkbenchEnvironmentService,
 		@INotificationService private readonly notificationService: INotificationService,
+		@IProgressService private readonly progressService: IProgressService,
 		@IDialogService private readonly dialogService: IDialogService,
 		@ICommandService private readonly commandService: ICommandService,
 		@IContextKeyService contextKeyService: IContextKeyService,
@@ -219,18 +221,31 @@ export class UserDataSyncWorkbenchService extends Disposable implements IUserDat
 			throw new Error(localize('no account', "No account available"));
 		}
 
-		const pullFirst = await this.handleFirstTimeSync();
-		await this.userDataAutoSyncService.turnOn(pullFirst);
-		this.notificationService.info(localize('sync turned on', "Preferences sync is turned on"));
+		const preferencesSyncTitle = localize('preferences sync', "Preferences Sync");
+		const title = `${preferencesSyncTitle} [(${localize('details', "details")})](command:${SHOW_SYNC_LOG_COMMAND_ID})`;
+		await this.progressService.withProgress({
+			location: ProgressLocation.Notification,
+			title,
+			delay: 500,
+		}, async (progress) => {
+			progress.report({ message: localize('turning on', "Turning on...") });
+			const pullFirst = await this.isSyncingWithAnotherMachine();
+			const disposable = this.userDataSyncService.onSynchronizeResource(resource =>
+				progress.report({ message: localize('syncing resource', "Syncing {0}...", getSyncAreaLabel(resource)) }));
+			await this.userDataAutoSyncService.turnOn(pullFirst);
+			disposable.dispose();
+		});
+
+		this.notificationService.info(localize('sync turned on', "{0} is turned on", title));
 	}
 
 	turnoff(everywhere: boolean): Promise<void> {
 		return this.userDataAutoSyncService.turnOff(everywhere);
 	}
 
-	private async handleFirstTimeSync(): Promise<boolean> {
-		const isFirstTimeSyncingWithAnotherMachine = await this.userDataSyncService.isFirstTimeSyncingWithAnotherMachine();
-		if (!isFirstTimeSyncingWithAnotherMachine) {
+	private async isSyncingWithAnotherMachine(): Promise<boolean> {
+		const isSyncingWithAnotherMachine = await this.userDataSyncService.isFirstTimeSyncingWithAnotherMachine();
+		if (!isSyncingWithAnotherMachine) {
 			return false;
 		}
 
diff --git a/src/vs/workbench/services/userDataSync/electron-browser/userDataSyncService.ts b/src/vs/workbench/services/userDataSync/electron-browser/userDataSyncService.ts
index a562eb0c66f..7f1084593fe 100644
--- a/src/vs/workbench/services/userDataSync/electron-browser/userDataSyncService.ts
+++ b/src/vs/workbench/services/userDataSync/electron-browser/userDataSyncService.ts
@@ -38,6 +38,8 @@ export class UserDataSyncService extends Disposable implements IUserDataSyncServ
 	private _onSyncErrors: Emitter<[SyncResource, UserDataSyncError][]> = this._register(new Emitter<[SyncResource, UserDataSyncError][]>());
 	readonly onSyncErrors: Event<[SyncResource, UserDataSyncError][]> = this._onSyncErrors.event;
 
+	get onSynchronizeResource(): Event<SyncResource> { return this.channel.listen<SyncResource>('onSynchronizeResource'); }
+
 	constructor(
 		@ISharedProcessService sharedProcessService: ISharedProcessService
 	) {