diff --git a/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts b/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts
index 544d8373b92..a0e58a18477 100644
--- a/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts
+++ b/src/vs/workbench/services/userDataSync/browser/userDataSyncWorkbenchService.ts
@@ -168,9 +168,16 @@ export class UserDataSyncWorkbenchService extends Disposable implements IUserDat
 
 	private async initialize(): Promise<void> {
 		const authenticationSession = await getCurrentAuthenticationSessionInfo(this.credentialsService, this.productService);
-		if (this.currentSessionId === undefined && this.useWorkbenchSessionId && authenticationSession?.id) {
-			this.currentSessionId = authenticationSession?.id;
-			this.useWorkbenchSessionId = !!this.environmentService.options?.settingsSyncOptions?.enabled;
+		if (this.currentSessionId === undefined && authenticationSession?.id) {
+			if (this.environmentService.options?.settingsSyncOptions?.authenticationProvider && this.environmentService.options.settingsSyncOptions.enabled) {
+				this.currentSessionId = authenticationSession?.id;
+			}
+
+			// Backward compatibility
+			else if (this.useWorkbenchSessionId) {
+				this.currentSessionId = authenticationSession?.id;
+			}
+			this.useWorkbenchSessionId = false;
 		}
 
 		await this.update();