diff --git a/src/vs/workbench/api/browser/mainThreadAuthentication.ts b/src/vs/workbench/api/browser/mainThreadAuthentication.ts
index 29460ca8c928a..f1916ddf3f6e9 100644
--- a/src/vs/workbench/api/browser/mainThreadAuthentication.ts
+++ b/src/vs/workbench/api/browser/mainThreadAuthentication.ts
@@ -34,7 +34,8 @@ const BUILT_IN_AUTH_DEPENDENTS: AuthDependent[] = [
 
 export class MainThreadAuthenticationProvider extends Disposable {
 	private _sessionMenuItems = new Map<string, IDisposable[]>();
-	private _sessionIds: string[] = [];
+	private _accounts = new Map<string, string[]>(); // Map account name to session ids
+	private _sessions = new Map<string, string>(); // Map account id to name
 
 	constructor(
 		private readonly _proxy: ExtHostAuthenticationShape,
@@ -44,10 +45,6 @@ export class MainThreadAuthenticationProvider extends Disposable {
 	) {
 		super();
 
-		if (!dependents.length) {
-			return;
-		}
-
 		this.registerCommandsAndContextMenuItems();
 	}
 
@@ -86,21 +83,23 @@ export class MainThreadAuthenticationProvider extends Disposable {
 	}
 
 	private registerCommandsAndContextMenuItems(): void {
-		this._register(CommandsRegistry.registerCommand({
-			id: `signIn${this.id}`,
-			handler: (accessor, args) => {
-				this.setPermissionsForAccount(accessor.get(IQuickInputService), true);
-			},
-		}));
-
-		this._register(MenuRegistry.appendMenuItem(MenuId.AccountsContext, {
-			group: '2_providers',
-			command: {
+		if (this.dependents.length) {
+			this._register(CommandsRegistry.registerCommand({
 				id: `signIn${this.id}`,
-				title: nls.localize('addAccount', "Sign in to {0}", this.displayName)
-			},
-			order: 3
-		}));
+				handler: (accessor, args) => {
+					this.setPermissionsForAccount(accessor.get(IQuickInputService), true);
+				},
+			}));
+
+			this._register(MenuRegistry.appendMenuItem(MenuId.AccountsContext, {
+				group: '2_providers',
+				command: {
+					id: `signIn${this.id}`,
+					title: nls.localize('addAccount', "Sign in to {0}", this.displayName)
+				},
+				order: 3
+			}));
+		}
 
 		this._proxy.$getSessions(this.id).then(sessions => {
 			sessions.forEach(session => this.registerSession(session));
@@ -108,7 +107,16 @@ export class MainThreadAuthenticationProvider extends Disposable {
 	}
 
 	private registerSession(session: modes.AuthenticationSession) {
-		this._sessionIds.push(session.id);
+		this._sessions.set(session.id, session.accountName);
+
+		const existingSessionsForAccount = this._accounts.get(session.accountName);
+		if (existingSessionsForAccount) {
+			this._accounts.set(session.accountName, existingSessionsForAccount.concat(session.id));
+			return;
+		} else {
+			this._accounts.set(session.accountName, [session.id]);
+		}
+
 		const menuItem = MenuRegistry.appendMenuItem(MenuId.AccountsContext, {
 			group: '1_accounts',
 			command: {
@@ -131,7 +139,8 @@ export class MainThreadAuthenticationProvider extends Disposable {
 				quickPick.onDidAccept(e => {
 					const selected = quickPick.selectedItems[0];
 					if (selected.label === 'Sign Out') {
-						this.logout(session.id);
+						const sessionsForAccount = this._accounts.get(session.accountName);
+						sessionsForAccount?.forEach(sessionId => this.logout(sessionId));
 					}
 
 					quickPick.dispose();
@@ -145,7 +154,7 @@ export class MainThreadAuthenticationProvider extends Disposable {
 			},
 		});
 
-		this._sessionMenuItems.set(session.id, [menuItem, manageCommand]);
+		this._sessionMenuItems.set(session.accountName, [menuItem, manageCommand]);
 	}
 
 	async getSessions(): Promise<ReadonlyArray<modes.AuthenticationSession>> {
@@ -158,22 +167,29 @@ export class MainThreadAuthenticationProvider extends Disposable {
 		});
 	}
 
-	async updateSessionItems(): Promise<void> {
-		const currentSessions = await this._proxy.$getSessions(this.id);
-		const removedSessionIds = this._sessionIds.filter(id => !currentSessions.some(session => session.id === id));
-		const addedSessions = currentSessions.filter(session => !this._sessionIds.some(id => id === session.id));
-
-		removedSessionIds.forEach(id => {
-			const disposeables = this._sessionMenuItems.get(id);
-			if (disposeables) {
-				disposeables.forEach(disposeable => disposeable.dispose());
-				this._sessionMenuItems.delete(id);
+	async updateSessionItems(event: modes.AuthenticationSessionsChangeEvent): Promise<void> {
+		const { added, removed } = event;
+		const session = await this._proxy.$getSessions(this.id);
+		const addedSessions = session.filter(session => added.some(id => id === session.id));
+
+		removed.forEach(sessionId => {
+			const accountName = this._sessions.get(sessionId);
+			if (accountName) {
+				let sessionsForAccount = this._accounts.get(accountName) || [];
+				const sessionIndex = sessionsForAccount.indexOf(sessionId);
+				sessionsForAccount.splice(sessionIndex);
+
+				if (!sessionsForAccount.length) {
+					const disposeables = this._sessionMenuItems.get(accountName);
+					if (disposeables) {
+						disposeables.forEach(disposeable => disposeable.dispose());
+						this._sessionMenuItems.delete(accountName);
+					}
+				}
 			}
 		});
 
 		addedSessions.forEach(session => this.registerSession(session));
-
-		this._sessionIds = currentSessions.map(session => session.id);
 	}
 
 	login(scopes: string[]): Promise<modes.AuthenticationSession> {
diff --git a/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts b/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
index 065099a486fdd..0d14030700496 100644
--- a/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
+++ b/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
@@ -53,6 +53,7 @@ import { IProductService } from 'vs/platform/product/common/productService';
 import { IStorageService, StorageScope } from 'vs/platform/storage/common/storage';
 import { IOpenerService } from 'vs/platform/opener/common/opener';
 import { timeout } from 'vs/base/common/async';
+import { distinct } from 'vs/base/common/arrays';
 
 const enum AuthStatus {
 	Initializing = 'Initializing',
@@ -251,7 +252,8 @@ export class UserDataSyncWorkbenchContribution extends Disposable implements IWo
 			const quickPick = this.quickInputService.createQuickPick<{ label: string, session: AuthenticationSession }>();
 			quickPick.title = localize('chooseAccountTitle', "Preferences Sync: Choose Account");
 			quickPick.placeholder = localize('chooseAccount', "Choose an account you would like to use for settings sync");
-			quickPick.items = sessions.map(session => {
+			const dedupedSessions = distinct(sessions, (session) => session.accountName);
+			quickPick.items = dedupedSessions.map(session => {
 				return {
 					label: session.accountName,
 					session: session
diff --git a/src/vs/workbench/services/authentication/browser/authenticationService.ts b/src/vs/workbench/services/authentication/browser/authenticationService.ts
index 4bb4455575321..69ae38aff8fc4 100644
--- a/src/vs/workbench/services/authentication/browser/authenticationService.ts
+++ b/src/vs/workbench/services/authentication/browser/authenticationService.ts
@@ -88,7 +88,7 @@ export class AuthenticationService extends Disposable implements IAuthentication
 		this._onDidChangeSessions.fire({ providerId: id, event: event });
 		const provider = this._authenticationProviders.get(id);
 		if (provider) {
-			provider.updateSessionItems();
+			provider.updateSessionItems(event);
 		}
 	}