diff --git a/src/vs/workbench/services/runtimeSession/common/runtimeSession.ts b/src/vs/workbench/services/runtimeSession/common/runtimeSession.ts
index 2af31f2a661..ec9d2016eab 100644
--- a/src/vs/workbench/services/runtimeSession/common/runtimeSession.ts
+++ b/src/vs/workbench/services/runtimeSession/common/runtimeSession.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as nls from 'vs/nls';
-import { DeferredPromise } from 'vs/base/common/async';
+import { DeferredPromise, disposableTimeout } from 'vs/base/common/async';
 import { Emitter } from 'vs/base/common/event';
 import { Disposable, DisposableStore, IDisposable, toDisposable } from 'vs/base/common/lifecycle';
 import { URI } from 'vs/base/common/uri';
@@ -377,33 +377,30 @@ export class RuntimeSessionService extends Disposable implements IRuntimeSession
 
 		// We wait for `onDidEndSession()` rather than `RuntimeState.Exited`, because the former
 		// generates some Console output that must finish before starting up a new runtime:
-		let disposable: IDisposable | undefined;
-		const promise = new Promise<void>(resolve => {
-			disposable = sessionDisposables.add(session.onDidEndSession((exit) => {
+		const disposables = sessionDisposables.add(new DisposableStore());
+		const promise = new Promise<void>((resolve, reject) => {
+			disposables.add(session.onDidEndSession((exit) => {
+				disposables.dispose();
 				resolve();
-				disposable?.dispose();
 			}));
-		});
-
-		const timeout = new Promise<void>((_, reject) => {
-			setTimeout(() => {
-				disposable?.dispose();
+			disposables.add(disposableTimeout(() => {
+				disposables.dispose();
 				reject(new Error(`Timed out waiting for runtime ` +
 					`${formatLanguageRuntimeSession(session)} to finish exiting.`));
-			}, 5000);
+			}, 5000));
 		});
 
 		// Ask the runtime to shut down.
 		try {
 			await session.shutdown(exitReason);
-		} catch (err) {
-			disposable?.dispose();
-			throw err;
+		} catch (error) {
+			disposables.dispose();
+			throw error;
 		}
 
 		// Wait for the runtime onDidEndSession to resolve, or for the timeout to expire
 		// (whichever comes first)
-		await Promise.race([promise, timeout]);
+		await promise;
 	}
 
 	/**
diff --git a/src/vs/workbench/services/runtimeSession/test/common/runtimeSession.test.ts b/src/vs/workbench/services/runtimeSession/test/common/runtimeSession.test.ts
index 482473a2077..85aa3b003ee 100644
--- a/src/vs/workbench/services/runtimeSession/test/common/runtimeSession.test.ts
+++ b/src/vs/workbench/services/runtimeSession/test/common/runtimeSession.test.ts
@@ -12,7 +12,7 @@ import { IConfigurationService } from 'vs/platform/configuration/common/configur
 import { TestConfigurationService } from 'vs/platform/configuration/test/common/testConfigurationService';
 import { TestInstantiationService } from 'vs/platform/instantiation/test/common/instantiationServiceMock';
 import { IWorkspaceTrustManagementService } from 'vs/platform/workspace/common/workspaceTrust';
-import { formatLanguageRuntimeMetadata, ILanguageRuntimeMetadata, ILanguageRuntimeService, LanguageRuntimeSessionMode, RuntimeExitReason, RuntimeState } from 'vs/workbench/services/languageRuntime/common/languageRuntimeService';
+import { formatLanguageRuntimeMetadata, formatLanguageRuntimeSession, ILanguageRuntimeMetadata, ILanguageRuntimeService, LanguageRuntimeSessionMode, RuntimeExitReason, RuntimeState } from 'vs/workbench/services/languageRuntime/common/languageRuntimeService';
 import { ILanguageRuntimeSession, IRuntimeSessionMetadata, IRuntimeSessionService, IRuntimeSessionWillStartEvent } from 'vs/workbench/services/runtimeSession/common/runtimeSessionService';
 import { TestLanguageRuntimeSession, waitForRuntimeState } from 'vs/workbench/services/runtimeSession/test/common/testLanguageRuntimeSession';
 import { createRuntimeServices, createTestLanguageRuntimeMetadata, startTestLanguageRuntimeSession } from 'vs/workbench/services/runtimeSession/test/common/testRuntimeSessionService';
@@ -653,6 +653,35 @@ suite('Positron - RuntimeSessionService', () => {
 		assert.equal(runtimeSessionService.foregroundSession, session1);
 	});
 
+	test(`select console to another runtime and first session never fires onDidEndSession`, async () => {
+		const session = await startConsole();
+		await waitForRuntimeState(session, RuntimeState.Ready);
+
+		// Stub onDidEndSession to never fire, causing the shutdown to time out.
+		sinon.stub(session, 'onDidEndSession').returns({ dispose: () => { } });
+
+		// Use a fake timer to avoid actually having to wait for the timeout.
+		const clock = sinon.useFakeTimers();
+		const promise = assert.rejects(selectRuntime(anotherRuntime), new Error(`Timed out waiting for runtime ` +
+			`${formatLanguageRuntimeSession(session)} to finish exiting.`));
+		await clock.tickAsync(10_000);
+		await promise;
+	});
+
+	test(`select console to another runtime encounters session.shutdown() error`, async () => {
+		const session = await startConsole();
+
+		// Stub session.shutdown() to throw an error.
+		const error = new Error('Session failed to shut down');
+		sinon.stub(session, 'shutdown').rejects(error);
+
+		// We also want to ensure that the timeout is not hit in this case but don't want to
+		// actually wait, so we use a fake timer.
+		const clock = sinon.useFakeTimers();
+		await assert.rejects(selectRuntime(anotherRuntime), error);
+		await clock.tickAsync(10_000);
+	});
+
 	function restartSession(sessionId: string) {
 		return runtimeSessionService.restartSession(sessionId, startReason);
 	}