diff --git a/src/messages.ts b/src/messages.ts
index 110d08d..ae1cb54 100644
--- a/src/messages.ts
+++ b/src/messages.ts
@@ -2,6 +2,7 @@ import type { MessageItem } from 'vscode';
 import { ConfigurationTarget, window } from 'vscode';
 import { configuration, SuppressedMessages } from './configuration';
 import { Commands } from './constants';
+import type { Container } from './container';
 import type { GitCommit } from './git/models/commit';
 import { Logger } from './logger';
 import { executeCommand } from './system/command';
@@ -172,6 +173,24 @@ export function showIntegrationRequestTimedOutWarningMessage(providerName: strin
 	);
 }
 
+export async function showProDiscountNotification(container: Container): Promise<void> {
+	if (container.storage.get('plus:discountNotificationShown', false)) return;
+
+	void container.storage.store('plus:discountNotificationShown', true);
+
+	const upgrade: MessageItem = { title: 'Upgrade to Pro' };
+	const result = await showMessage(
+		'info',
+		'GitLens Pro introductory pricing, up to a 60% discount, goes away tomorrow. Upgrade to GitLens Pro now to access [GitLens+ features](command:gitlens.plus.learn) on private repos at a reduced rate.',
+		undefined,
+		undefined,
+		upgrade,
+	);
+	if (result === upgrade) {
+		void container.subscription.purchase();
+	}
+}
+
 export async function showWhatsNewMessage(version: string) {
 	const whatsnew = { title: "See What's New" };
 	const result = await showMessage(
diff --git a/src/plus/subscription/subscriptionService.ts b/src/plus/subscription/subscriptionService.ts
index 3d28c22..13c7c0b 100644
--- a/src/plus/subscription/subscriptionService.ts
+++ b/src/plus/subscription/subscriptionService.ts
@@ -27,6 +27,7 @@ import { setContext } from '../../context';
 import { AccountValidationError } from '../../errors';
 import type { RepositoriesChangeEvent } from '../../git/gitProviderService';
 import { Logger } from '../../logger';
+import { showProDiscountNotification } from '../../messages';
 import type { Subscription } from '../../subscription';
 import {
 	computeSubscriptionState,
@@ -843,6 +844,16 @@ export class SubscriptionService implements Disposable {
 		this._subscription = subscription;
 		this._etag = Date.now();
 
+		setTimeout(() => {
+			if (
+				new Date() < new Date('2022-10-18T00:00:00.000Z') &&
+				subscription!.account != null &&
+				!isSubscriptionPaid(subscription!)
+			) {
+				void showProDiscountNotification(this.container);
+			}
+		}, 5000);
+
 		if (!silent) {
 			this.updateContext();
 
diff --git a/src/storage.ts b/src/storage.ts
index c34495d..5d96e6b 100644
--- a/src/storage.ts
+++ b/src/storage.ts
@@ -144,6 +144,7 @@ export interface GlobalStorage {
 	pendingWhatsNewOnFocus?: boolean;
 	plus: {
 		migratedAuthentication?: boolean;
+		discountNotificationShown?: boolean;
 	};
 	// Don't change this key name ('premium`) as its the stored subscription
 	premium: {