diff --git a/src/vs/workbench/electron-sandbox/window.ts b/src/vs/workbench/electron-sandbox/window.ts
index 323316af370be..cf6af9debb4aa 100644
--- a/src/vs/workbench/electron-sandbox/window.ts
+++ b/src/vs/workbench/electron-sandbox/window.ts
@@ -697,23 +697,44 @@ export class NativeWindow extends Disposable {
 			}
 		}
 
-		// Windows 7 warning
+		// Windows 7/8/8.1 warning
 		if (isWindows) {
 			const version = this.environmentService.os.release.split('.');
+			const majorVersion = version[0];
+			const minorVersion = version[1];
+			const eolReleases = new Map<string, Map<string, string>>([
+				['6', new Map<string, string>([
+					['1', 'Windows 7 / Windows Server 2008 R2'],
+					['2', 'Windows 8 / Windows Server 2012'],
+					['3', 'Windows 8.1 / Windows Server 2012 R2'],
+				])],
+			]);
 
 			// Refs https://docs.microsoft.com/en-us/windows/win32/api/winnt/ns-winnt-osversioninfoa
-			if (parseInt(version[0]) === 6 && parseInt(version[1]) === 1) {
-				const message = localize('windows 7 eol', "{0} on Windows 7 will no longer receive any further updates.", this.productService.nameLong);
+			if (eolReleases.get(majorVersion)?.has(minorVersion)) {
+				const message = localize('windowseolmessage', "{0} on {1} will soon stop receiving updates. Consider upgrading your windows version.", this.productService.nameLong, eolReleases.get(majorVersion)?.get(minorVersion));
+				const actions = [{
+					label: localize('windowseolBannerLearnMore', "Learn More"),
+					href: 'https://aka.ms/vscode-faq-old-windows'
+				}];
+
+				this.bannerService.show({
+					id: 'windowseol.banner',
+					message,
+					ariaLabel: localize('windowseolarialabel', "{0}. Use navigation keys to access banner actions.", message),
+					actions,
+					icon: Codicon.warning
+				});
 
 				this.notificationService.prompt(
 					Severity.Warning,
 					message,
 					[{
 						label: localize('learnMore', "Learn More"),
-						run: () => this.openerService.open(URI.parse('https://aka.ms/vscode-faq-win7'))
+						run: () => this.openerService.open(URI.parse('https://aka.ms/vscode-faq-old-windows'))
 					}],
 					{
-						neverShowAgain: { id: 'windows7eol', isSecondary: true, scope: NeverShowAgainScope.APPLICATION },
+						neverShowAgain: { id: 'windowseol', isSecondary: true, scope: NeverShowAgainScope.APPLICATION },
 						priority: NotificationPriority.URGENT,
 						sticky: true
 					}