diff --git a/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStarted.contribution.ts b/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStarted.contribution.ts
index 45c1b9e55af..bd80f2e53ae 100644
--- a/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStarted.contribution.ts
+++ b/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStarted.contribution.ts
@@ -15,7 +15,7 @@ import { KeybindingWeight } from 'vs/platform/keybinding/common/keybindingsRegis
 import { KeyCode, KeyMod } from 'vs/base/common/keyCodes';
 import { EditorDescriptor, IEditorRegistry } from 'vs/workbench/browser/editor';
 import { SyncDescriptor } from 'vs/platform/instantiation/common/descriptors';
-import { IGettingStartedNewMenuEntryDescriptorCategory, IGettingStartedService } from 'vs/workbench/contrib/welcome/gettingStarted/browser/gettingStartedService';
+import { HasMultipleNewFileEntries, IGettingStartedNewMenuEntryDescriptorCategory, IGettingStartedService } from 'vs/workbench/contrib/welcome/gettingStarted/browser/gettingStartedService';
 import { GettingStartedInput } from 'vs/workbench/contrib/welcome/gettingStarted/browser/gettingStartedInput';
 import { Extensions as WorkbenchExtensions, IWorkbenchContributionsRegistry } from 'vs/workbench/common/contributions';
 import { LifecyclePhase } from 'vs/workbench/services/lifecycle/common/lifecycle';
@@ -199,6 +199,7 @@ registerAction2(class extends Action2 {
 			},
 			menu: {
 				id: MenuId.MenubarFileMenu,
+				when: HasMultipleNewFileEntries,
 				group: '1_new',
 				order: 3
 			}
diff --git a/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStartedService.ts b/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStartedService.ts
index c74ad120827..f6bdff48359 100644
--- a/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStartedService.ts
+++ b/src/vs/workbench/contrib/welcome/gettingStarted/browser/gettingStartedService.ts
@@ -36,6 +36,7 @@ import { IQuickInputService, IQuickPickItem, IQuickPickSeparator } from 'vs/plat
 import { IKeybindingService } from 'vs/platform/keybinding/common/keybinding';
 
 export const WorkspacePlatform = new RawContextKey<'mac' | 'linux' | 'windows' | undefined>('workspacePlatform', undefined, localize('workspacePlatform', "The platform of the current workspace, which in remote contexts may be different from the platform of the UI"));
+export const HasMultipleNewFileEntries = new RawContextKey<boolean>('hasMultipleNewFileEntries', false);
 
 export const IGettingStartedService = createDecorator<IGettingStartedService>('gettingStartedService');
 
@@ -309,6 +310,8 @@ export class GettingStartedService extends Disposable implements IGettingStarted
 			e.affectedKeys.forEach(key => { this.progressByEvent('onSettingChanged:' + key); });
 		}));
 
+		HasMultipleNewFileEntries.bindTo(this.contextService).set(false);
+
 		this.remoteAgentService.getEnvironment().then(env => {
 			const remoteOS = env?.os;
 
@@ -672,6 +675,10 @@ export class GettingStartedService extends Disposable implements IGettingStarted
 	private registerNewMenuItem(categoryDescriptor: IGettingStartedNewMenuEntryDescriptor) {
 		this.newMenuItems.push(categoryDescriptor);
 		this.newMenuItems.sort((a, b) => b.category - a.category);
+		if (categoryDescriptor.category === IGettingStartedNewMenuEntryDescriptorCategory.file || categoryDescriptor.category === IGettingStartedNewMenuEntryDescriptorCategory.notebook) {
+			HasMultipleNewFileEntries.bindTo(this.contextService).set(true);
+		}
+
 		this._onDidAddNewEntry.fire();
 	}
 
@@ -697,6 +704,11 @@ export class GettingStartedService extends Disposable implements IGettingStarted
 		}
 
 		this.newMenuItems = this.newMenuItems.filter(entry => entry.sourceExtensionId !== extension.identifier.value);
+		HasMultipleNewFileEntries.bindTo(this.contextService).set(
+			this.newMenuItems.filter(entry =>
+				entry.category === IGettingStartedNewMenuEntryDescriptorCategory.file
+				|| entry.category === IGettingStartedNewMenuEntryDescriptorCategory.notebook).length > 1
+		);
 	}
 
 	private registerDoneListeners(step: IGettingStartedStep) {