diff --git a/src/vs/workbench/api/browser/mainThreadDebugService.ts b/src/vs/workbench/api/browser/mainThreadDebugService.ts
index 79fe81e21d6..6b833ab272e 100644
--- a/src/vs/workbench/api/browser/mainThreadDebugService.ts
+++ b/src/vs/workbench/api/browser/mainThreadDebugService.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { DisposableStore } from 'vs/base/common/lifecycle';
+import { DisposableStore, toDisposable } from 'vs/base/common/lifecycle';
 import { URI as uri, UriComponents } from 'vs/base/common/uri';
 import { IDebugService, IConfig, IDebugConfigurationProvider, IBreakpoint, IFunctionBreakpoint, IBreakpointData, IDebugAdapter, IDebugAdapterDescriptorFactory, IDebugSession, IDebugAdapterFactory, IDataBreakpoint, IDebugSessionOptions, IInstructionBreakpoint, DebugConfigurationProviderTriggerKind } from 'vs/workbench/contrib/debug/common/debug';
 import {
@@ -50,6 +50,11 @@ export class MainThreadDebugService implements MainThreadDebugServiceShape, IDeb
 		this._toDispose.add(debugService.getViewModel().onDidFocusSession(session => {
 			this._proxy.$acceptDebugSessionActiveChanged(this.getSessionDto(session));
 		}));
+		this._toDispose.add(toDisposable(() => {
+			for (const [handle, da] of this._debugAdapters) {
+				da.fireError(handle, new Error('Extension host shut down'));
+			}
+		}));
 
 		this._debugAdapters = new Map();
 		this._debugConfigurationProviders = new Map();
diff --git a/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts b/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts
index 294aaffa3e9..db8cd73120e 100644
--- a/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts
+++ b/src/vs/workbench/contrib/debug/browser/rawDebugSession.ts
@@ -573,7 +573,8 @@ export class RawDebugSession implements IDisposable {
 						args.suspendDebuggee = suspendDebuggee;
 					}
 
-					await this.send('disconnect', args, undefined, 2000);
+					// if there's an error, the DA is probably already gone, so give it a much shorter timeout.
+					await this.send('disconnect', args, undefined, error ? 200 : 2000);
 				} catch (e) {
 					// Catch the potential 'disconnect' error - no need to show it to the user since the adapter is shutting down
 				} finally {