diff --git a/extensions/microsoft-authentication/src/common/telemetryReporter.ts b/extensions/microsoft-authentication/src/common/telemetryReporter.ts
index c28aa887e0c..e18c743de9b 100644
--- a/extensions/microsoft-authentication/src/common/telemetryReporter.ts
+++ b/extensions/microsoft-authentication/src/common/telemetryReporter.ts
@@ -35,6 +35,13 @@ export class MicrosoftAuthenticationTelemetryReporter implements IExperimentatio
 		);
 	}
 
+	sendActivatedWithClassicImplementationEvent(): void {
+		/* __GDPR__
+			"activatingClassic" : { "owner": "TylerLeonhardt", "comment": "Used to determine how often users use the classic login flow." }
+		*/
+		this._telemetryReporter.sendTelemetryEvent('activatingClassic');
+	}
+
 	sendLoginEvent(scopes: readonly string[]): void {
 		/* __GDPR__
 			"login" : {
diff --git a/extensions/microsoft-authentication/src/extension.ts b/extensions/microsoft-authentication/src/extension.ts
index bd32a82290a..6a5fac9765d 100644
--- a/extensions/microsoft-authentication/src/extension.ts
+++ b/extensions/microsoft-authentication/src/extension.ts
@@ -48,14 +48,12 @@ export async function activate(context: ExtensionContext) {
 		env.uriScheme !== 'vscode', // isPreRelease
 	);
 	useMsal = shouldUseMsal(expService);
-	const clientIdVersion = workspace.getConfiguration('microsoft-authentication').get<'v1' | 'v2'>('clientIdVersion', 'v1');
-
 	context.subscriptions.push(workspace.onDidChangeConfiguration(async e => {
 		if (!e.affectsConfiguration('microsoft-authentication')) {
 			return;
 		}
 
-		if (useMsal === shouldUseMsal(expService) && clientIdVersion === workspace.getConfiguration('microsoft-authentication').get<'v1' | 'v2'>('clientIdVersion', 'v1')) {
+		if (useMsal === shouldUseMsal(expService)) {
 			return;
 		}
 
@@ -77,6 +75,7 @@ export async function activate(context: ExtensionContext) {
 	if (useMsal && typeof navigator === 'undefined') {
 		await extensionV2.activate(context, mainTelemetryReporter);
 	} else {
+		mainTelemetryReporter.sendActivatedWithClassicImplementationEvent();
 		await extensionV1.activate(context, mainTelemetryReporter.telemetryReporter);
 	}
 }