diff --git a/src/vs/workbench/api/browser/mainThreadAuthentication.ts b/src/vs/workbench/api/browser/mainThreadAuthentication.ts
index ef09b13eb17..eae11fc5843 100644
--- a/src/vs/workbench/api/browser/mainThreadAuthentication.ts
+++ b/src/vs/workbench/api/browser/mainThreadAuthentication.ts
@@ -251,7 +251,9 @@ export class MainThreadAuthentication extends Disposable implements MainThreadAu
 				throw new Error('User did not consent to login.');
 			}
 
-			const session = await this.authenticationService.createSession(providerId, scopes, true);
+			const session = sessions?.length && !options.forceNewSession
+				? await this.authenticationService.selectSession(providerId, extensionId, extensionName, scopes, sessions)
+				: await this.authenticationService.createSession(providerId, scopes, true);
 			await this.setTrustedExtensionAndAccountPreference(providerId, session.account.label, extensionId, extensionName, session.id);
 			return session;
 		}
diff --git a/src/vs/workbench/test/browser/api/extHostAuthentication.test.ts b/src/vs/workbench/test/browser/api/extHostAuthentication.test.ts
index aa5e63baa4d..260ea31ca98 100644
--- a/src/vs/workbench/test/browser/api/extHostAuthentication.test.ts
+++ b/src/vs/workbench/test/browser/api/extHostAuthentication.test.ts
@@ -63,6 +63,9 @@ class TestAuthProvider implements AuthenticationProvider {
 			return [...this.sessions.values()];
 		}
 
+		if (scopes[0] === 'return multiple') {
+			return [...this.sessions.values()];
+		}
 		const sessions = this.sessions.get(scopes.join(' '));
 		return sessions ? [sessions] : [];
 	}
@@ -70,7 +73,7 @@ class TestAuthProvider implements AuthenticationProvider {
 		const scopesStr = scopes.join(' ');
 		const session = {
 			scopes,
-			id: 'test',
+			id: 'test' + scopesStr,
 			account: {
 				label: scopesStr,
 				id: scopesStr,
@@ -126,22 +129,24 @@ suite('ExtHostAuthentication', () => {
 	});
 
 	test('createIfNone - true', async () => {
+		const scopes = ['foo'];
 		const session = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				createIfNone: true
 			});
-		assert.strictEqual(session?.id, 'test');
+		assert.strictEqual(session?.id, 'test' + scopes.join(' '));
 		assert.strictEqual(session?.scopes[0], 'foo');
 	});
 
 	test('createIfNone - false', async () => {
+		const scopes = ['foo'];
 		const nosession = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{});
 		assert.strictEqual(nosession, undefined);
 
@@ -149,18 +154,18 @@ suite('ExtHostAuthentication', () => {
 		const session = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				createIfNone: true
 			});
 
-		assert.strictEqual(session?.id, 'test');
+		assert.strictEqual(session?.id, 'test' + scopes.join(' '));
 		assert.strictEqual(session?.scopes[0], 'foo');
 
 		const session2 = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{});
 
 		assert.strictEqual(session.id, session2?.id);
@@ -170,10 +175,11 @@ suite('ExtHostAuthentication', () => {
 
 	// should behave the same as createIfNone: false
 	test('silent - true', async () => {
+		const scopes = ['foo'];
 		const nosession = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				silent: true
 			});
@@ -183,18 +189,18 @@ suite('ExtHostAuthentication', () => {
 		const session = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				createIfNone: true
 			});
 
-		assert.strictEqual(session?.id, 'test');
+		assert.strictEqual(session?.id, 'test' + scopes.join(' '));
 		assert.strictEqual(session?.scopes[0], 'foo');
 
 		const session2 = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				silent: true
 			});
@@ -204,10 +210,11 @@ suite('ExtHostAuthentication', () => {
 	});
 
 	test('forceNewSession - true', async () => {
+		const scopes = ['foo'];
 		const session1 = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				createIfNone: true
 			});
@@ -216,21 +223,22 @@ suite('ExtHostAuthentication', () => {
 		const session2 = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				forceNewSession: true
 			});
 
-		assert.strictEqual(session2?.id, 'test');
+		assert.strictEqual(session2?.id, 'test' + scopes.join(' '));
 		assert.strictEqual(session2?.scopes[0], 'foo');
 		assert.notStrictEqual(session1.accessToken, session2?.accessToken);
 	});
 
 	test('forceNewSession - detail', async () => {
+		const scopes = ['foo'];
 		const session1 = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				createIfNone: true
 			});
@@ -239,41 +247,55 @@ suite('ExtHostAuthentication', () => {
 		const session2 = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test',
-			['foo'],
+			scopes,
 			{
 				forceNewSession: { detail: 'bar' }
 			});
 
-		assert.strictEqual(session2?.id, 'test');
+		assert.strictEqual(session2?.id, 'test' + scopes.join(' '));
 		assert.strictEqual(session2?.scopes[0], 'foo');
 		assert.notStrictEqual(session1.accessToken, session2?.accessToken);
 	});
 
 	test('clearSessionPreference - true', async () => {
+		const scopes = ['foo'];
 		// Now create the session
 		const session = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test-multiple',
-			['foo'],
+			scopes,
 			{
 				createIfNone: true
 			});
 
-		assert.strictEqual(session?.id, 'test');
-		assert.strictEqual(session?.scopes[0], 'foo');
+		assert.strictEqual(session?.id, 'test' + scopes.join(' '));
+		assert.strictEqual(session?.scopes[0], scopes[0]);
 
+		const scopes2 = ['bar'];
 		const session2 = await extHostAuthentication.getSession(
 			extensionDescription,
 			'test-multiple',
-			['foo'],
+			scopes2,
+			{
+				createIfNone: true
+			});
+		assert.strictEqual(session2?.id, 'test' + scopes2.join(' '));
+		assert.strictEqual(session2?.scopes[0], scopes2[0]);
+
+		const session3 = await extHostAuthentication.getSession(
+			extensionDescription,
+			'test-multiple',
+			['return multiple'],
 			{
 				clearSessionPreference: true,
 				createIfNone: true
 			});
 
-		assert.strictEqual(session.id, session2?.id);
-		assert.strictEqual(session.scopes[0], session2?.scopes[0]);
-		assert.notStrictEqual(session.accessToken, session2?.accessToken);
+		// clearing session preference causes us to get the first session
+		// because it would normally show a quick pick for the user to choose
+		assert.strictEqual(session.id, session3?.id);
+		assert.strictEqual(session.scopes[0], session3?.scopes[0]);
+		assert.strictEqual(session.accessToken, session3?.accessToken);
 	});
 
 	//#region error cases