diff --git a/extensions/vscode-account/src/AADHelper.ts b/extensions/vscode-account/src/AADHelper.ts
index ab523e39929..94bc3695dc4 100644
--- a/extensions/vscode-account/src/AADHelper.ts
+++ b/extensions/vscode-account/src/AADHelper.ts
@@ -274,9 +274,9 @@ export class AzureActiveDirectoryService {
 				res.writeHead(302, { Location: '/' });
 				res.end();
 			} catch (err) {
-				Logger.error(err.message);
 				res.writeHead(302, { Location: `/?error=${encodeURIComponent(err && err.message || 'Unknown error')}` });
 				res.end();
+				throw new Error(err.message);
 			}
 		} catch (e) {
 			Logger.error(e.message);
@@ -285,6 +285,7 @@ export class AzureActiveDirectoryService {
 			if (e.message === 'Error listening to server' || e.message === 'Closed' || e.message === 'Timeout waiting for port') {
 				await this.loginWithoutLocalServer(scope);
 			}
+			throw new Error(e.message);
 		} finally {
 			setTimeout(() => {
 				server.close();
diff --git a/extensions/vscode-account/src/extension.ts b/extensions/vscode-account/src/extension.ts
index 7d896b01d6a..36c2d4a02df 100644
--- a/extensions/vscode-account/src/extension.ts
+++ b/extensions/vscode-account/src/extension.ts
@@ -22,7 +22,6 @@ export async function activate(_: vscode.ExtensionContext) {
 				await loginService.login(scopes.sort().join(' '));
 				return loginService.sessions[0]!;
 			} catch (e) {
-				vscode.window.showErrorMessage(`Logging in failed: ${e}`);
 				throw e;
 			}
 		},
diff --git a/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts b/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
index 1d5486d52ab..3c4f49387b8 100644
--- a/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
+++ b/src/vs/workbench/contrib/userDataSync/browser/userDataSync.ts
@@ -569,7 +569,7 @@ export class UserDataSyncWorkbenchContribution extends Disposable implements IWo
 		try {
 			await this.setActiveAccount(await this.authenticationService.login(this.userDataSyncStore!.authenticationProviderId, ['https://management.core.windows.net/.default', 'offline_access']));
 		} catch (e) {
-			this.notificationService.error(e);
+			this.notificationService.error(localize('loginFailed', "Logging in failed: {0}", e));
 			throw e;
 		}
 	}