diff --git a/src/vs/workbench/services/extensionManagement/browser/extensionEnablementService.ts b/src/vs/workbench/services/extensionManagement/browser/extensionEnablementService.ts
index d6191e89c6e5c..4ac057e34da04 100644
--- a/src/vs/workbench/services/extensionManagement/browser/extensionEnablementService.ts
+++ b/src/vs/workbench/services/extensionManagement/browser/extensionEnablementService.ts
@@ -25,7 +25,7 @@ import { ILifecycleService, LifecyclePhase } from 'vs/workbench/services/lifecyc
 import { INotificationService, Severity } from 'vs/platform/notification/common/notification';
 import { IHostService } from 'vs/workbench/services/host/browser/host';
 import { IExtensionBisectService } from 'vs/workbench/services/extensionManagement/browser/extensionBisect';
-import { IWorkspaceTrustService, WorkspaceTrustState } from 'vs/platform/workspace/common/workspaceTrust';
+import { IWorkspaceTrustService, WorkspaceTrustState, WorkspaceTrustStateChangeEvent } from 'vs/platform/workspace/common/workspaceTrust';
 import { Promises } from 'vs/base/common/async';
 
 const SOURCE = 'IWorkbenchExtensionEnablementService';
@@ -64,18 +64,13 @@ export class ExtensionEnablementService extends Disposable implements IWorkbench
 		this._register(this.globalExtensionEnablementService.onDidChangeEnablement(({ extensions, source }) => this.onDidChangeExtensions(extensions, source)));
 		this._register(extensionManagementService.onDidInstallExtension(this._onDidInstallExtension, this));
 		this._register(extensionManagementService.onDidUninstallExtension(this._onDidUninstallExtension, this));
+		this._register(this.workspaceTrustService.onDidChangeTrustState(this._onDidChangeTrustState, this));
 
 		// Trusted extensions notification
 		// TODO: Confirm that this is the right lifecycle phase
 		this.lifecycleService.when(LifecyclePhase.Eventually).then(() => {
 			if (this.extensionsDisabledByTrustRequirement.length > 0) {
-				this.workspaceTrustService.requireWorkspaceTrust({ modal: false })
-					.then(trustState => {
-						if (trustState === WorkspaceTrustState.Trusted) {
-							this._onEnablementChanged.fire(this.extensionsDisabledByTrustRequirement);
-							this.extensionsDisabledByTrustRequirement = [];
-						}
-					});
+				this.workspaceTrustService.requireWorkspaceTrust({ modal: false });
 			}
 		});
 
@@ -447,7 +442,8 @@ export class ExtensionEnablementService extends Disposable implements IWorkbench
 
 	private _onDidInstallExtension({ local, error }: DidInstallExtensionEvent): void {
 		if (local && !error && this._isDisabledByTrustRequirement(local)) {
-			this.workspaceTrustService.requireWorkspaceTrust();
+			this.workspaceTrustService.requireWorkspaceTrust({ modal: false });
+			this._onEnablementChanged.fire([local]);
 		}
 	}
 
@@ -457,6 +453,13 @@ export class ExtensionEnablementService extends Disposable implements IWorkbench
 		}
 	}
 
+	private _onDidChangeTrustState({ currentTrustState }: WorkspaceTrustStateChangeEvent): void {
+		if (currentTrustState === WorkspaceTrustState.Trusted && this.extensionsDisabledByTrustRequirement.length > 0) {
+			this._onEnablementChanged.fire(this.extensionsDisabledByTrustRequirement);
+			this.extensionsDisabledByTrustRequirement = [];
+		}
+	}
+
 	private _reset(extension: IExtensionIdentifier) {
 		this._removeFromWorkspaceDisabledExtensions(extension);
 		this._removeFromWorkspaceEnabledExtensions(extension);
diff --git a/src/vs/workbench/services/extensionManagement/common/extensionManagementService.ts b/src/vs/workbench/services/extensionManagement/common/extensionManagementService.ts
index 91eea651c1c46..5577f0072a176 100644
--- a/src/vs/workbench/services/extensionManagement/common/extensionManagementService.ts
+++ b/src/vs/workbench/services/extensionManagement/common/extensionManagementService.ts
@@ -25,7 +25,7 @@ import Severity from 'vs/base/common/severity';
 import { canceled } from 'vs/base/common/errors';
 import { IUserDataAutoSyncEnablementService, IUserDataSyncResourceEnablementService, SyncResource } from 'vs/platform/userDataSync/common/userDataSync';
 import { Promises } from 'vs/base/common/async';
-import { IWorkspaceTrustService, WorkspaceTrustState } from 'vs/platform/workspace/common/workspaceTrust';
+import { IWorkspaceTrustService } from 'vs/platform/workspace/common/workspaceTrust';
 
 export class ExtensionManagementService extends Disposable implements IWorkbenchExtensionManagementService {
 
@@ -362,8 +362,21 @@ export class ExtensionManagementService extends Disposable implements IWorkbench
 
 	protected async checkForWorkspaceTrust(manifest: IExtensionManifest): Promise<void> {
 		if (getExtensionWorkspaceTrustRequirement(manifest) === 'onStart') {
-			const trustState = await this.workspaceTrustService.requireWorkspaceTrust();
-			return trustState === WorkspaceTrustState.Trusted ? Promise.resolve() : Promise.reject(canceled());
+			try {
+				await this.workspaceTrustService.requireWorkspaceTrust({
+					modal: true,
+					message: localize('extensionInstallWorkspaceTrustMessage', "Enabling this extension requires a trusted workspace."),
+					buttons: [
+						{ label: localize('extensionInstallWorkspaceTrustButton', "Trust Workspace & Install"), type: 'ContinueWithTrust' },
+						{ label: localize('extensionInstallWorkspaceTrustContinueButton', "Install"), type: 'ContinueWithoutTrust' },
+						{ label: localize('extensionInstallWorkspaceTrustManageButton', "Learn More"), type: 'Manage' }
+					]
+				});
+				return Promise.resolve();
+			}
+			catch (error) {
+				return Promise.reject(error);
+			}
 		}
 		return Promise.resolve();
 	}