diff --git a/src/vs/platform/userDataProfile/common/userDataProfile.ts b/src/vs/platform/userDataProfile/common/userDataProfile.ts
index 1d3cc902349..9df1359aed6 100644
--- a/src/vs/platform/userDataProfile/common/userDataProfile.ts
+++ b/src/vs/platform/userDataProfile/common/userDataProfile.ts
@@ -225,6 +225,10 @@ export class UserDataProfilesService extends Disposable implements IUserDataProf
 	}
 
 	getProfile(workspaceIdentifier: WorkspaceIdentifier, profileToUseIfNotSet: IUserDataProfile): IUserDataProfile {
+		if (!this.enabled) {
+			return this.defaultProfile;
+		}
+
 		const workspace = this.getWorkspace(workspaceIdentifier);
 		let profile = URI.isUri(workspace) ? this.profilesObject.workspaces.get(workspace) : this.profilesObject.emptyWindow;
 		if (!profile) {
diff --git a/src/vs/workbench/browser/web.main.ts b/src/vs/workbench/browser/web.main.ts
index b36b008adce..2e744b847fa 100644
--- a/src/vs/workbench/browser/web.main.ts
+++ b/src/vs/workbench/browser/web.main.ts
@@ -269,7 +269,9 @@ export class BrowserMain extends Disposable {
 		// User Data Profiles
 		const userDataProfilesService = new BrowserUserDataProfilesService(environmentService, fileService, uriIdentityService, logService);
 		serviceCollection.set(IUserDataProfilesService, userDataProfilesService);
-		const userDataProfileService = new UserDataProfileService(userDataProfilesService.getProfile(isWorkspaceIdentifier(payload) || isSingleFolderWorkspaceIdentifier(payload) ? payload : 'empty-window', userDataProfilesService.defaultProfile), userDataProfilesService);
+		const lastActiveProfile = environmentService.lastActiveProfile ? userDataProfilesService.profiles.find(p => p.id === environmentService.lastActiveProfile) : undefined;
+		const currentProfile = userDataProfilesService.getProfile(isWorkspaceIdentifier(payload) || isSingleFolderWorkspaceIdentifier(payload) ? payload : 'empty-window', lastActiveProfile ?? userDataProfilesService.defaultProfile);
+		const userDataProfileService = new UserDataProfileService(currentProfile, userDataProfilesService);
 		serviceCollection.set(IUserDataProfileService, userDataProfileService);
 
 		// Long running services (workspace, config, storage)
diff --git a/src/vs/workbench/services/environment/browser/environmentService.ts b/src/vs/workbench/services/environment/browser/environmentService.ts
index 122eba1dec7..1ed00644937 100644
--- a/src/vs/workbench/services/environment/browser/environmentService.ts
+++ b/src/vs/workbench/services/environment/browser/environmentService.ts
@@ -208,6 +208,9 @@ export class BrowserWorkbenchEnvironmentService implements IBrowserWorkbenchEnvi
 	@memoize
 	get disableWorkspaceTrust(): boolean { return !this.options.enableWorkspaceTrust; }
 
+	@memoize
+	get lastActiveProfile(): string | undefined { return this.payload?.get('lastActiveProfile'); }
+
 	editSessionId: string | undefined = this.options.editSessionId;
 
 	private payload: Map<string, string> | undefined;
diff --git a/src/vs/workbench/services/host/browser/browserHostService.ts b/src/vs/workbench/services/host/browser/browserHostService.ts
index 25fca6a0136..efba94ca42a 100644
--- a/src/vs/workbench/services/host/browser/browserHostService.ts
+++ b/src/vs/workbench/services/host/browser/browserHostService.ts
@@ -35,6 +35,7 @@ import { isTemporaryWorkspace, IWorkspaceContextService } from 'vs/platform/work
 import { ServicesAccessor } from 'vs/editor/browser/editorExtensions';
 import { Schemas } from 'vs/base/common/network';
 import { ITextEditorOptions } from 'vs/platform/editor/common/editor';
+import { IUserDataProfileService } from 'vs/workbench/services/userDataProfile/common/userDataProfile';
 
 /**
  * A workspace to open in the workbench can either be:
@@ -112,7 +113,8 @@ export class BrowserHostService extends Disposable implements IHostService {
 		@ILifecycleService private readonly lifecycleService: BrowserLifecycleService,
 		@ILogService private readonly logService: ILogService,
 		@IDialogService private readonly dialogService: IDialogService,
-		@IWorkspaceContextService private readonly contextService: IWorkspaceContextService
+		@IWorkspaceContextService private readonly contextService: IWorkspaceContextService,
+		@IUserDataProfileService private readonly userDataProfileService: IUserDataProfileService,
 	) {
 		super();
 
@@ -214,7 +216,7 @@ export class BrowserHostService extends Disposable implements IHostService {
 	}
 
 	private async doOpenWindow(toOpen: IWindowOpenable[], options?: IOpenWindowOptions): Promise<void> {
-		const payload = this.preservePayload();
+		const payload = this.preservePayload(false /* not an empty window */);
 		const fileOpenables: IFileToOpen[] = [];
 		const foldersToAdd: IWorkspaceFolderCreationData[] = [];
 
@@ -371,13 +373,11 @@ export class BrowserHostService extends Disposable implements IHostService {
 		this.instantiationService.invokeFunction(accessor => fn(accessor));
 	}
 
-	private preservePayload(): Array<unknown> | undefined {
+	private preservePayload(isEmptyWindow: boolean): Array<unknown> | undefined {
 
 		// Selectively copy payload: for now only extension debugging properties are considered
-		let newPayload: Array<unknown> | undefined = undefined;
-		if (this.environmentService.extensionDevelopmentLocationURI) {
-			newPayload = new Array();
-
+		const newPayload: Array<unknown> = new Array();
+		if (!isEmptyWindow && this.environmentService.extensionDevelopmentLocationURI) {
 			newPayload.push(['extensionDevelopmentPath', this.environmentService.extensionDevelopmentLocationURI.toString()]);
 
 			if (this.environmentService.debugExtensionHost.debugId) {
@@ -389,7 +389,11 @@ export class BrowserHostService extends Disposable implements IHostService {
 			}
 		}
 
-		return newPayload;
+		if (!this.userDataProfileService.currentProfile.isDefault) {
+			newPayload.push(['lastActiveProfile', this.userDataProfileService.currentProfile.id]);
+		}
+
+		return newPayload.length ? newPayload : undefined;
 	}
 
 	private getRecentLabel(openable: IWindowOpenable): string {
@@ -421,7 +425,10 @@ export class BrowserHostService extends Disposable implements IHostService {
 	}
 
 	private async doOpenEmptyWindow(options?: IOpenEmptyWindowOptions): Promise<void> {
-		return this.doOpen(undefined, { reuse: options?.forceReuseWindow });
+		return this.doOpen(undefined, {
+			reuse: options?.forceReuseWindow,
+			payload: this.preservePayload(true /* empty window */)
+		});
 	}
 
 	private async doOpen(workspace: IWorkspace, options?: { reuse?: boolean; payload?: object }): Promise<void> {