diff --git a/extensions/vscode-test-resolver/src/extension.ts b/extensions/vscode-test-resolver/src/extension.ts
index 99d3619e316..c338957146b 100644
--- a/extensions/vscode-test-resolver/src/extension.ts
+++ b/extensions/vscode-test-resolver/src/extension.ts
@@ -203,7 +203,8 @@ export function activate(context: vscode.ExtensionContext) {
 				proxyServer.listen(0, () => {
 					const port = (<net.AddressInfo>proxyServer.address()).port;
 					outputChannel.appendLine(`Going through proxy at port ${port}`);
-					res(new vscode.ResolvedAuthority('127.0.0.1', port));
+					const r: vscode.ResolverResult = new vscode.ResolvedAuthority('127.0.0.1', port);
+					res(r);
 				});
 				context.subscriptions.push({
 					dispose: () => {
diff --git a/src/vs/platform/remote/common/remoteAuthorityResolver.ts b/src/vs/platform/remote/common/remoteAuthorityResolver.ts
index 163eb7223c0..52902edfcbc 100644
--- a/src/vs/platform/remote/common/remoteAuthorityResolver.ts
+++ b/src/vs/platform/remote/common/remoteAuthorityResolver.ts
@@ -18,12 +18,12 @@ export interface ResolvedAuthority {
 export enum RemoteTrustOption {
 	Unknown = 0,
 	DisableTrust = 1,
-	MachineTrusted = 2,
-	MachineUntrusted = 3
+	MachineTrusted = 2
 }
 
 export interface ResolvedOptions {
 	readonly extensionHostEnv?: { [key: string]: string | null };
+	readonly trust?: RemoteTrustOption;
 }
 
 export interface TunnelDescription {
diff --git a/src/vs/vscode.proposed.d.ts b/src/vs/vscode.proposed.d.ts
index 8bf049a5403..a8a8d826f6f 100644
--- a/src/vs/vscode.proposed.d.ts
+++ b/src/vs/vscode.proposed.d.ts
@@ -83,8 +83,7 @@ declare module 'vscode' {
 	export enum RemoteTrustOption {
 		Unknown = 0,
 		DisableTrust = 1,
-		MachineTrusted = 2,
-		MachineUntrusted = 3
+		MachineTrusted = 2
 	}
 
 	export interface ResolvedOptions {
diff --git a/src/vs/workbench/api/common/extHostExtensionService.ts b/src/vs/workbench/api/common/extHostExtensionService.ts
index 56f193da7fa..757dacc932c 100644
--- a/src/vs/workbench/api/common/extHostExtensionService.ts
+++ b/src/vs/workbench/api/common/extHostExtensionService.ts
@@ -668,7 +668,8 @@ export abstract class AbstractExtHostExtensionService extends Disposable impleme
 				connectionToken: result.connectionToken
 			};
 			const options: ResolvedOptions = {
-				extensionHostEnv: result.extensionHostEnv
+				extensionHostEnv: result.extensionHostEnv,
+				trust: result.trust
 			};
 
 			return {
diff --git a/src/vs/workbench/services/extensions/electron-browser/extensionService.ts b/src/vs/workbench/services/extensions/electron-browser/extensionService.ts
index 20f334886e0..a20ccff1632 100644
--- a/src/vs/workbench/services/extensions/electron-browser/extensionService.ts
+++ b/src/vs/workbench/services/extensions/electron-browser/extensionService.ts
@@ -15,7 +15,7 @@ import { IWorkbenchExtensionEnablementService, EnablementState, IWebExtensionsSc
 import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
 import { IRemoteExtensionHostDataProvider, RemoteExtensionHost, IRemoteExtensionHostInitData } from 'vs/workbench/services/extensions/common/remoteExtensionHost';
 import { IRemoteAgentService } from 'vs/workbench/services/remote/common/remoteAgentService';
-import { IRemoteAuthorityResolverService, RemoteAuthorityResolverError, ResolverResult } from 'vs/platform/remote/common/remoteAuthorityResolver';
+import { IRemoteAuthorityResolverService, RemoteAuthorityResolverError, RemoteTrustOption, ResolverResult } from 'vs/platform/remote/common/remoteAuthorityResolver';
 import { IInstantiationService, ServicesAccessor } from 'vs/platform/instantiation/common/instantiation';
 import { ILifecycleService, LifecyclePhase } from 'vs/workbench/services/lifecycle/common/lifecycle';
 import { INotificationService, Severity } from 'vs/platform/notification/common/notification';
@@ -44,6 +44,7 @@ import { updateProxyConfigurationsScope } from 'vs/platform/request/common/reque
 import { ConfigurationScope } from 'vs/platform/configuration/common/configurationRegistry';
 import { Codicon } from 'vs/base/common/codicons';
 import { IDialogService } from 'vs/platform/dialogs/common/dialogs';
+import { IWorkspaceTrustManagementService } from 'vs/platform/workspace/common/workspaceTrust';
 
 const MACHINE_PROMPT = false;
 
@@ -74,6 +75,7 @@ export class ExtensionService extends AbstractExtensionService implements IExten
 		@IExtensionGalleryService private readonly _extensionGalleryService: IExtensionGalleryService,
 		@ILogService private readonly _logService: ILogService,
 		@IDialogService private readonly _dialogService: IDialogService,
+		@IWorkspaceTrustManagementService private readonly _workspaceTrustManagementService: IWorkspaceTrustManagementService,
 	) {
 		super(
 			new ExtensionRunningLocationClassifier(
@@ -363,11 +365,20 @@ export class ExtensionService extends AbstractExtensionService implements IExten
 				return;
 			}
 
-			if (MACHINE_PROMPT) {
+			let promptForMachineTrust = MACHINE_PROMPT;
+
+			if (resolverResult.options?.trust === RemoteTrustOption.DisableTrust) {
+				promptForMachineTrust = false;
+				this._workspaceTrustManagementService.setWorkspaceTrust(true);
+			} else if (resolverResult.options?.trust === RemoteTrustOption.MachineTrusted) {
+				promptForMachineTrust = false;
+			}
+
+			if (promptForMachineTrust) {
 				const dialogResult = await this._dialogService.show(
 					Severity.Info,
 					nls.localize('machineTrustQuestion', "Do you trust the machine you're connecting to?"),
-					[nls.localize('yes', "Yes, connect."), nls.localize('no', "No, disconnect.")],
+					[nls.localize('yes', "Yes, connect."), nls.localize('no', "No, do not connect.")],
 					{
 						cancelId: 1,
 						custom: {