fixes #33452

src/vs/workbench/parts/debug/browser/debugActions.ts

@@ -118,9 +118,8 @@ export class StartAction extends AbstractDebugAction {
 		@IWorkspaceContextService private contextService: IWorkspaceContextService
 	) {
 		super(id, label, 'debug-action start', debugService, keybindingService);
-		this.debugService.getConfigurationManager().onDidSelectConfiguration(() => {
-			this.updateEnablement();
-		});
+		this.debugService.getConfigurationManager().onDidSelectConfiguration(() => this.updateEnablement());
+		this.debugService.getModel().onDidChangeCallStack(() => this.updateEnablement());
 	}
 
 	public run(): TPromise<any> {

src/vs/workbench/parts/debug/electron-browser/debugService.ts

@@ -873,6 +873,9 @@ export class DebugService implements debug.IDebugService {
 				if (!session.disconnected) {
 					session.disconnect().done(null, errors.onUnexpectedError);
 				}
+				if (process) {
+					this.model.removeProcess(process.getId());
+				}
 				// Show the repl if some error got logged there #5870
 				if (this.model.getReplElements().length > 0) {
 					this.panelService.openPanel(debug.REPL_ID, false).done(undefined, errors.onUnexpectedError);