diff --git a/src/vs/workbench/contrib/debug/browser/debug.contribution.ts b/src/vs/workbench/contrib/debug/browser/debug.contribution.ts
index a09e3d739c1..d9572ef3095 100644
--- a/src/vs/workbench/contrib/debug/browser/debug.contribution.ts
+++ b/src/vs/workbench/contrib/debug/browser/debug.contribution.ts
@@ -55,6 +55,7 @@ import { DisassemblyView, DisassemblyViewContribution } from 'vs/workbench/contr
 import { EditorPaneDescriptor, IEditorPaneRegistry } from 'vs/workbench/browser/editor';
 import { DisassemblyViewInput } from 'vs/workbench/contrib/debug/common/disassemblyViewInput';
 import { Codicon } from 'vs/base/common/codicons';
+import { DebugLifecycle } from 'vs/workbench/contrib/debug/common/debugLifecycle';
 
 const debugCategory = nls.localize('debugCategory', "Debug");
 registerColors();
@@ -70,6 +71,7 @@ Registry.as<IWorkbenchContributionsRegistry>(WorkbenchExtensions.Workbench).regi
 Registry.as<IWorkbenchContributionsRegistry>(WorkbenchExtensions.Workbench).registerWorkbenchContribution(DebugContentProvider, LifecyclePhase.Eventually);
 Registry.as<IWorkbenchContributionsRegistry>(WorkbenchExtensions.Workbench).registerWorkbenchContribution(StatusBarColorProvider, LifecyclePhase.Eventually);
 Registry.as<IWorkbenchContributionsRegistry>(WorkbenchExtensions.Workbench).registerWorkbenchContribution(DisassemblyViewContribution, LifecyclePhase.Eventually);
+Registry.as<IWorkbenchContributionsRegistry>(WorkbenchExtensions.Workbench).registerWorkbenchContribution(DebugLifecycle, LifecyclePhase.Eventually);
 
 // Register Quick Access
 Registry.as<IQuickAccessRegistry>(QuickAccessExtensions.Quickaccess).registerQuickAccessProvider({
@@ -524,6 +526,16 @@ configurationRegistry.registerConfiguration({
 			],
 			default: 'allEditorsInActiveGroup',
 			scope: ConfigurationScope.LANGUAGE_OVERRIDABLE
+		},
+		'debug.confirmOnExit': {
+			description: nls.localize('debug.confirmOnExit', "Controls whether to confirm when the window closes if there are active debug sessions."),
+			type: 'string',
+			enum: ['never', 'always'],
+			enumDescriptions: [
+				nls.localize('debug.confirmOnExit.never', "Never confirm."),
+				nls.localize('debug.confirmOnExit.always', "Always confirm if there are debug sessions."),
+			],
+			default: 'never'
 		}
 	}
 });
diff --git a/src/vs/workbench/contrib/debug/common/debug.ts b/src/vs/workbench/contrib/debug/common/debug.ts
index c585d8131aa..ea4e5c14fc1 100644
--- a/src/vs/workbench/contrib/debug/common/debug.ts
+++ b/src/vs/workbench/contrib/debug/common/debug.ts
@@ -547,6 +547,7 @@ export interface IDebugConfiguration {
 	onTaskErrors: 'debugAnyway' | 'showErrors' | 'prompt' | 'abort';
 	showBreakpointsInOverviewRuler: boolean;
 	showInlineBreakpointCandidates: boolean;
+	confirmOnExit: 'always' | 'never';
 }
 
 export interface IGlobalConfig {
diff --git a/src/vs/workbench/contrib/debug/common/debugLifecycle.ts b/src/vs/workbench/contrib/debug/common/debugLifecycle.ts
new file mode 100644
index 00000000000..5cce9304f75
--- /dev/null
+++ b/src/vs/workbench/contrib/debug/common/debugLifecycle.ts
@@ -0,0 +1,50 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as nls from 'vs/nls';
+import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
+import { IDialogService } from 'vs/platform/dialogs/common/dialogs';
+import { IWorkbenchContribution } from 'vs/workbench/common/contributions';
+import { IDebugConfiguration, IDebugService } from 'vs/workbench/contrib/debug/common/debug';
+import { ILifecycleService, ShutdownReason } from 'vs/workbench/services/lifecycle/common/lifecycle';
+
+export class DebugLifecycle implements IWorkbenchContribution {
+	constructor(
+		@ILifecycleService lifecycleService: ILifecycleService,
+		@IDebugService private readonly debugService: IDebugService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IDialogService private readonly dialogService: IDialogService,
+	) {
+		lifecycleService.onBeforeShutdown(async e => e.veto(this.shouldVetoShutdown(e.reason), 'veto.debug'));
+	}
+
+	private shouldVetoShutdown(_reason: ShutdownReason): boolean | Promise<boolean> {
+		const rootSessions = this.debugService.getModel().getSessions().filter(s => s.parentSession === undefined);
+		if (rootSessions.length === 0) {
+			return false;
+		}
+
+		const shouldConfirmOnExit = this.configurationService.getValue<IDebugConfiguration>('debug').confirmOnExit;
+		if (shouldConfirmOnExit === 'never') {
+			return false;
+		}
+
+		return this._showWindowCloseConfirmation(rootSessions.length);
+	}
+
+	protected async _showWindowCloseConfirmation(numSessions: number): Promise<boolean> {
+		let message: string;
+		if (numSessions === 1) {
+			message = nls.localize('debug.debugSessionCloseConfirmationSingular', "There is an active debug session, are you sure you want to terminate it?");
+		} else {
+			message = nls.localize('debug.debugSessionCloseConfirmationPlural', "There are active debug sessions, are you sure you want to terminate them?");
+		}
+		const res = await this.dialogService.confirm({
+			message,
+			type: 'warning',
+		});
+		return !res.confirmed;
+	}
+}