diff --git a/src/vs/platform/userDataSync/common/userDataAutoSyncService.ts b/src/vs/platform/userDataSync/common/userDataAutoSyncService.ts
index 62dd7cc144c41..cb5c8d665f718 100644
--- a/src/vs/platform/userDataSync/common/userDataAutoSyncService.ts
+++ b/src/vs/platform/userDataSync/common/userDataAutoSyncService.ts
@@ -219,8 +219,14 @@ export class UserDataAutoSyncService extends UserDataAutoSyncEnablementService i
 			this.telemetryService.publicLog2<{ code: string }, AutoSyncErrorClassification>(`autosync/error`, { code: userDataSyncError.code });
 		}
 
-		// Turned off from another device or session got expired
-		if (userDataSyncError.code === UserDataSyncErrorCode.TurnedOff || userDataSyncError.code === UserDataSyncErrorCode.SessionExpired) {
+		// Session got expired
+		if (userDataSyncError.code === UserDataSyncErrorCode.SessionExpired) {
+			await this.turnOff(false, true /* force soft turnoff on error */);
+			this.logService.info('Auto Sync: Turned off sync because current session is expired');
+		}
+
+		// Turned off from another device
+		if (userDataSyncError.code === UserDataSyncErrorCode.TurnedOff) {
 			await this.turnOff(false, true /* force soft turnoff on error */);
 			this.logService.info('Auto Sync: Turned off sync because sync is turned off in the cloud');
 		}
diff --git a/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts b/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
index a7db7c25c79f3..436487eab2fee 100644
--- a/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
+++ b/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
@@ -270,11 +270,19 @@ export class UserDataSyncWorkbenchContribution extends Disposable implements IWo
 
 	private onAutoSyncError(error: UserDataSyncError): void {
 		switch (error.code) {
-			case UserDataSyncErrorCode.TurnedOff:
 			case UserDataSyncErrorCode.SessionExpired:
 				this.notificationService.notify({
 					severity: Severity.Info,
-					message: localize('turned off', "Preferences sync was turned off from another device."),
+					message: localize('session expired', "Preferences sync was turned off because current session is expired, please sign in again to turn on sync."),
+					actions: {
+						primary: [new Action('turn on sync', localize('turn on sync', "Turn on Preferences Sync..."), undefined, true, () => this.turnOn())]
+					}
+				});
+				break;
+			case UserDataSyncErrorCode.TurnedOff:
+				this.notificationService.notify({
+					severity: Severity.Info,
+					message: localize('turned off', "Preferences sync was turned off from another device, please sign in again to turn on sync."),
 					actions: {
 						primary: [new Action('turn on sync', localize('turn on sync', "Turn on Preferences Sync..."), undefined, true, () => this.turnOn())]
 					}