diff --git a/extensions/github-authentication/src/extension.ts b/extensions/github-authentication/src/extension.ts
index c9025e7373f..d2022806057 100644
--- a/extensions/github-authentication/src/extension.ts
+++ b/extensions/github-authentication/src/extension.ts
@@ -22,7 +22,7 @@ export async function activate(context: vscode.ExtensionContext) {
 		return loginService.manuallyProvideToken();
 	}));
 
-	vscode.authentication.registerAuthenticationProvider({
+	context.subscriptions.push(vscode.authentication.registerAuthenticationProvider({
 		id: 'github',
 		label: 'GitHub',
 		supportsMultipleAccounts: false,
@@ -70,7 +70,7 @@ export async function activate(context: vscode.ExtensionContext) {
 				throw e;
 			}
 		}
-	});
+	}));
 
 	return;
 }
diff --git a/src/vs/workbench/services/authentication/browser/authenticationService.ts b/src/vs/workbench/services/authentication/browser/authenticationService.ts
index 5b609209058..82a27ec5e0c 100644
--- a/src/vs/workbench/services/authentication/browser/authenticationService.ts
+++ b/src/vs/workbench/services/authentication/browser/authenticationService.ts
@@ -432,24 +432,46 @@ export class AuthenticationService extends Disposable implements IAuthentication
 		}
 	}
 
-	async getSessions(id: string): Promise<ReadonlyArray<AuthenticationSession>> {
-		await this.extensionService.activateByEvent(getAuthenticationProviderActivationEvent(id));
+	private async tryActivateProvider(providerId: string): Promise<MainThreadAuthenticationProvider> {
+		await this.extensionService.activateByEvent(getAuthenticationProviderActivationEvent(providerId));
+		let provider = this._authenticationProviders.get(providerId);
+		if (provider) {
+			return provider;
+		}
 
-		const authProvider = this._authenticationProviders.get(id);
-		if (authProvider) {
+		// When activate has completed, the extension has made the call to `registerAuthenticationProvider`.
+		// However, activate cannot block on this, so the renderer may not have gotten the event yet.
+		const didRegister: Promise<MainThreadAuthenticationProvider> = new Promise((resolve, _) => {
+			this.onDidRegisterAuthenticationProvider(e => {
+				if (e.id === providerId) {
+					resolve(this._authenticationProviders.get(providerId));
+				}
+			});
+		});
+
+		const didTimeout: Promise<MainThreadAuthenticationProvider> = new Promise((_, reject) => {
+			setTimeout(() => {
+				reject();
+			}, 2000);
+		});
+
+		return Promise.race([didRegister, didTimeout]);
+	}
+
+	async getSessions(id: string): Promise<ReadonlyArray<AuthenticationSession>> {
+		try {
+			const authProvider = this._authenticationProviders.get(id) || await this.tryActivateProvider(id);
 			return await authProvider.getSessions();
-		} else {
+		} catch (_) {
 			throw new Error(`No authentication provider '${id}' is currently registered.`);
 		}
 	}
 
 	async login(id: string, scopes: string[]): Promise<AuthenticationSession> {
-		await this.extensionService.activateByEvent(getAuthenticationProviderActivationEvent(id));
-
-		const authProvider = this._authenticationProviders.get(id);
-		if (authProvider) {
-			return authProvider.login(scopes);
-		} else {
+		try {
+			const authProvider = this._authenticationProviders.get(id) || await this.tryActivateProvider(id);
+			return await authProvider.login(scopes);
+		} catch (_) {
 			throw new Error(`No authentication provider '${id}' is currently registered.`);
 		}
 	}