diff --git a/src/vs/platform/environment/common/environment.ts b/src/vs/platform/environment/common/environment.ts
index f899de2f910..c6f9e804869 100644
--- a/src/vs/platform/environment/common/environment.ts
+++ b/src/vs/platform/environment/common/environment.ts
@@ -36,6 +36,10 @@ export interface IEnvironmentService {
 	argvResource: URI;
 	snippetsHome: URI;
 
+	// --- data paths
+	backupHome: URI;
+	untitledWorkspacesHome: URI;
+
 	// --- settings sync
 	userDataSyncLogResource: URI;
 	userDataSyncHome: URI;
@@ -56,20 +60,10 @@ export interface IEnvironmentService {
 	verbose: boolean;
 	isBuilt: boolean;
 
-	// --- data paths
-	backupHome: URI;
-	untitledWorkspacesHome: URI;
-
 	// --- misc
 	disableTelemetry: boolean;
-
 	serviceMachineIdResource: URI;
 
-	/**
-	 * @deprecated use IRemotePathService#userHome instead (https://github.com/microsoft/vscode/issues/94506)
-	 */
-	userHome?: URI;
-
 	// !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
 	// NOTE: DO NOT ADD ANY OTHER PROPERTY INTO THE COLLECTION HERE
 	// UNLESS THIS PROPERTY IS SUPPORTED BOTH IN WEB AND DESKTOP!!!!
diff --git a/src/vs/workbench/contrib/debug/browser/linkDetector.ts b/src/vs/workbench/contrib/debug/browser/linkDetector.ts
index 4319d66031c..32b3f73ec44 100644
--- a/src/vs/workbench/contrib/debug/browser/linkDetector.ts
+++ b/src/vs/workbench/contrib/debug/browser/linkDetector.ts
@@ -120,7 +120,7 @@ export class LinkDetector {
 		}
 
 		if (path[0] === '~') {
-			const userHome = this.remotePathService.userHomeSync;
+			const userHome = this.remotePathService.resolvedUserHome;
 			if (userHome) {
 				path = osPath.join(userHome.fsPath, path.substring(1));
 			}
diff --git a/src/vs/workbench/contrib/debug/browser/loadedScriptsView.ts b/src/vs/workbench/contrib/debug/browser/loadedScriptsView.ts
index 286099ff89a..700f7e611c8 100644
--- a/src/vs/workbench/contrib/debug/browser/loadedScriptsView.ts
+++ b/src/vs/workbench/contrib/debug/browser/loadedScriptsView.ts
@@ -347,7 +347,7 @@ class SessionTreeItem extends BaseTreeItem {
 				} else {
 					// on unix try to tildify absolute paths
 					path = normalize(path);
-					const userHome = this._remotePathService.userHomeSync;
+					const userHome = this._remotePathService.resolvedUserHome;
 					if (userHome && !isWindows) {
 						path = tildify(path, userHome.fsPath);
 					}
diff --git a/src/vs/workbench/contrib/search/browser/anythingQuickAccess.ts b/src/vs/workbench/contrib/search/browser/anythingQuickAccess.ts
index 717e3d4139b..753a608da79 100644
--- a/src/vs/workbench/contrib/search/browser/anythingQuickAccess.ts
+++ b/src/vs/workbench/contrib/search/browser/anythingQuickAccess.ts
@@ -631,7 +631,8 @@ export class AnythingQuickAccessProvider extends PickerQuickAccessProvider<IAnyt
 			return;
 		}
 
-		const detildifiedQuery = untildify(query.original, (await this.remotePathService.userHome).path);
+		const userHome = await this.remotePathService.userHome;
+		const detildifiedQuery = untildify(query.original, userHome.scheme === Schemas.file ? userHome.fsPath : userHome.path);
 		if (token.isCancellationRequested) {
 			return;
 		}
diff --git a/src/vs/workbench/contrib/search/common/queryBuilder.ts b/src/vs/workbench/contrib/search/common/queryBuilder.ts
index 6227e360e76..68071a2c0ac 100644
--- a/src/vs/workbench/contrib/search/common/queryBuilder.ts
+++ b/src/vs/workbench/contrib/search/common/queryBuilder.ts
@@ -12,7 +12,7 @@ import { Schemas } from 'vs/base/common/network';
 import * as path from 'vs/base/common/path';
 import { isEqual } from 'vs/base/common/resources';
 import * as strings from 'vs/base/common/strings';
-import { URI as uri, URI } from 'vs/base/common/uri';
+import { URI as uri } from 'vs/base/common/uri';
 import { isMultilineRegexSource } from 'vs/editor/common/model/textModelSearch';
 import * as nls from 'vs/nls';
 import { IConfigurationService } from 'vs/platform/configuration/common/configuration';
@@ -84,13 +84,8 @@ export class QueryBuilder {
 		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
 		@IRemotePathService private readonly remotePathService: IRemotePathService
 	) {
-		this.remotePathService.userHome.then(userHome => {
-			this._userHome = userHome;
-		});
 	}
 
-	private _userHome: URI | undefined;
-
 	text(contentPattern: IPatternInfo, folderResources?: uri[], options: ITextQueryBuilderOptions = {}): ITextQuery {
 		contentPattern = this.getContentPattern(contentPattern, options);
 		const searchConfig = this.configurationService.getValue<ISearchConfiguration>();
@@ -244,8 +239,9 @@ export class QueryBuilder {
 
 		const segments = splitGlobPattern(pattern)
 			.map(segment => {
-				if (this._userHome) {
-					return untildify(segment, this._userHome.fsPath);
+				const userHome = this.remotePathService.resolvedUserHome;
+				if (userHome) {
+					return untildify(segment, userHome.scheme === Schemas.file ? userHome.fsPath : userHome.path);
 				}
 
 				return segment;
diff --git a/src/vs/workbench/contrib/search/test/browser/queryBuilder.test.ts b/src/vs/workbench/contrib/search/test/browser/queryBuilder.test.ts
index cc8f788f891..27104feb755 100644
--- a/src/vs/workbench/contrib/search/test/browser/queryBuilder.test.ts
+++ b/src/vs/workbench/contrib/search/test/browser/queryBuilder.test.ts
@@ -50,7 +50,7 @@ suite('QueryBuilder', () => {
 
 		instantiationService.stub(IWorkspaceContextService, mockContextService);
 		instantiationService.stub(IEnvironmentService, TestEnvironmentService);
-		instantiationService.stub(IRemotePathService, new TestRemotePathService(TestEnvironmentService));
+		instantiationService.stub(IRemotePathService, new TestRemotePathService());
 
 		queryBuilder = instantiationService.createInstance(QueryBuilder);
 	});
diff --git a/src/vs/workbench/contrib/search/test/electron-browser/queryBuilder.test.ts b/src/vs/workbench/contrib/search/test/electron-browser/queryBuilder.test.ts
index bc60138cbbc..9a4980f43f0 100644
--- a/src/vs/workbench/contrib/search/test/electron-browser/queryBuilder.test.ts
+++ b/src/vs/workbench/contrib/search/test/electron-browser/queryBuilder.test.ts
@@ -8,10 +8,9 @@ import { IEnvironmentService } from 'vs/platform/environment/common/environment'
 import { TestInstantiationService } from 'vs/platform/instantiation/test/common/instantiationServiceMock';
 import { IWorkspaceContextService, toWorkspaceFolder, Workspace } from 'vs/platform/workspace/common/workspace';
 import { ISearchPathsInfo, QueryBuilder } from 'vs/workbench/contrib/search/common/queryBuilder';
-import { TestEnvironmentService } from 'vs/workbench/test/electron-browser/workbenchTestServices';
+import { TestEnvironmentService, TestNativeRemotePathService } from 'vs/workbench/test/electron-browser/workbenchTestServices';
 import { assertEqualSearchPathResults, getUri, patternsToIExpression, globalGlob, fixPath } from 'vs/workbench/contrib/search/test/browser/queryBuilder.test';
 import { TestContextService } from 'vs/workbench/test/common/workbenchTestServices';
-import { TestRemotePathService } from 'vs/workbench/test/browser/workbenchTestServices';
 import { IRemotePathService } from 'vs/workbench/services/path/common/remotePathService';
 
 const DEFAULT_EDITOR_CONFIG = {};
@@ -41,7 +40,7 @@ suite('QueryBuilder', () => {
 
 		instantiationService.stub(IWorkspaceContextService, mockContextService);
 		instantiationService.stub(IEnvironmentService, TestEnvironmentService);
-		instantiationService.stub(IRemotePathService, new TestRemotePathService(TestEnvironmentService));
+		instantiationService.stub(IRemotePathService, new TestNativeRemotePathService(TestEnvironmentService));
 
 		queryBuilder = instantiationService.createInstance(QueryBuilder);
 		await new Promise(resolve => setTimeout(resolve, 5)); // Wait for RemotePathService.userHome to resolve
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
index 2d67cee7dfa..e023fe1b214 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
@@ -135,9 +135,9 @@ export class TerminalProcessManager extends Disposable implements ITerminalProce
 			const hasRemoteAuthority = !!this.remoteAuthority;
 			let launchRemotely = hasRemoteAuthority || forceExtHostProcess;
 
-			// userHomeSync is needed here as remote resolvers can launch local terminals before
+			// resolvedUserHome is needed here as remote resolvers can launch local terminals before
 			// they're connected to the remote.
-			this.userHome = this._remotePathService.userHomeSync?.fsPath;
+			this.userHome = this._remotePathService.resolvedUserHome?.fsPath;
 			this.os = platform.OS;
 			if (launchRemotely) {
 				const userHomeUri = await this._remotePathService.userHome;
diff --git a/src/vs/workbench/contrib/terminal/test/browser/links/terminalLinkManager.test.ts b/src/vs/workbench/contrib/terminal/test/browser/links/terminalLinkManager.test.ts
index ad7fd6a94e6..5662066333d 100644
--- a/src/vs/workbench/contrib/terminal/test/browser/links/terminalLinkManager.test.ts
+++ b/src/vs/workbench/contrib/terminal/test/browser/links/terminalLinkManager.test.ts
@@ -93,7 +93,7 @@ suite('Workbench - TerminalLinkHandler', () => {
 	setup(() => {
 		instantiationService = new TestInstantiationService();
 		instantiationService.stub(IEnvironmentService, TestEnvironmentService);
-		instantiationService.stub(IRemotePathService, new TestRemotePathService(TestEnvironmentService));
+		instantiationService.stub(IRemotePathService, new TestRemotePathService());
 	});
 
 	suite('localLinkRegex', () => {
diff --git a/src/vs/workbench/services/keybinding/test/electron-browser/keybindingEditing.test.ts b/src/vs/workbench/services/keybinding/test/electron-browser/keybindingEditing.test.ts
index eb501abe939..5ef56f5c844 100644
--- a/src/vs/workbench/services/keybinding/test/electron-browser/keybindingEditing.test.ts
+++ b/src/vs/workbench/services/keybinding/test/electron-browser/keybindingEditing.test.ts
@@ -38,7 +38,7 @@ import { IEditorGroupsService } from 'vs/workbench/services/editor/common/editor
 import { KeybindingsEditingService } from 'vs/workbench/services/keybinding/common/keybindingEditing';
 import { ITextFileService } from 'vs/workbench/services/textfile/common/textfiles';
 import { TextModelResolverService } from 'vs/workbench/services/textmodelResolver/common/textModelResolverService';
-import { TestBackupFileService, TestEditorGroupsService, TestEditorService, TestLifecycleService } from 'vs/workbench/test/browser/workbenchTestServices';
+import { TestBackupFileService, TestEditorGroupsService, TestEditorService, TestLifecycleService, TestRemotePathService } from 'vs/workbench/test/browser/workbenchTestServices';
 import { FileService } from 'vs/platform/files/common/fileService';
 import { Schemas } from 'vs/base/common/network';
 import { DiskFileSystemProvider } from 'vs/platform/files/node/diskFileSystemProvider';
@@ -57,6 +57,7 @@ import { UndoRedoService } from 'vs/platform/undoRedo/common/undoRedoService';
 import { TestTextResourcePropertiesService, TestContextService, TestWorkingCopyService } from 'vs/workbench/test/common/workbenchTestServices';
 import { IThemeService } from 'vs/platform/theme/common/themeService';
 import { TestThemeService } from 'vs/platform/theme/test/common/testThemeService';
+import { IRemotePathService } from 'vs/workbench/services/path/common/remotePathService';
 
 class TestEnvironmentService extends NativeWorkbenchEnvironmentService {
 
@@ -93,6 +94,7 @@ suite('KeybindingsEditing', () => {
 			configService.setUserConfiguration('files', { 'eol': '\n' });
 
 			instantiationService.stub(IEnvironmentService, environmentService);
+			instantiationService.stub(IRemotePathService, new TestRemotePathService());
 			instantiationService.stub(IConfigurationService, configService);
 			instantiationService.stub(IWorkspaceContextService, new TestContextService());
 			const lifecycleService = new TestLifecycleService();
diff --git a/src/vs/workbench/services/label/common/labelService.ts b/src/vs/workbench/services/label/common/labelService.ts
index 74d17900862..3200d718844 100644
--- a/src/vs/workbench/services/label/common/labelService.ts
+++ b/src/vs/workbench/services/label/common/labelService.ts
@@ -135,7 +135,7 @@ export class LabelService extends Disposable implements ILabelService {
 
 	private doGetUriLabel(resource: URI, formatting?: ResourceLabelFormatting, options: { relative?: boolean, noPrefix?: boolean, endWithSeparator?: boolean } = {}): string {
 		if (!formatting) {
-			return getPathLabel(resource.path, this.environmentService, options.relative ? this.contextService : undefined);
+			return getPathLabel(resource.path, { userHome: this.remotePathService.resolvedUserHome }, options.relative ? this.contextService : undefined);
 		}
 
 		let label: string | undefined;
@@ -266,7 +266,7 @@ export class LabelService extends Disposable implements ILabelService {
 		}
 
 		if (formatting.tildify && !forceNoTildify) {
-			const userHome = this.remotePathService.userHomeSync;
+			const userHome = this.remotePathService.resolvedUserHome;
 			if (userHome) {
 				label = tildify(label, userHome.fsPath);
 			}
diff --git a/src/vs/workbench/services/label/test/browser/label.test.ts b/src/vs/workbench/services/label/test/browser/label.test.ts
index ddecfd5863b..76370016b78 100644
--- a/src/vs/workbench/services/label/test/browser/label.test.ts
+++ b/src/vs/workbench/services/label/test/browser/label.test.ts
@@ -5,10 +5,7 @@
 
 import * as assert from 'assert';
 import { TestEnvironmentService, TestRemotePathService } from 'vs/workbench/test/browser/workbenchTestServices';
-import { TestWorkspace } from 'vs/platform/workspace/test/common/testWorkspace';
 import { URI } from 'vs/base/common/uri';
-import { sep } from 'vs/base/common/path';
-import { isWindows } from 'vs/base/common/platform';
 import { LabelService } from 'vs/workbench/services/label/common/labelService';
 import { TestContextService } from 'vs/workbench/test/common/workbenchTestServices';
 
@@ -17,28 +14,7 @@ suite('URI Label', () => {
 	let labelService: LabelService;
 
 	setup(() => {
-		labelService = new LabelService(TestEnvironmentService, new TestContextService(), new TestRemotePathService(TestEnvironmentService));
-	});
-
-	test('file scheme', function () {
-		labelService.registerFormatter({
-			scheme: 'file',
-			formatting: {
-				label: '${path}',
-				separator: sep,
-				tildify: !isWindows,
-				normalizeDriveLetter: isWindows
-			}
-		});
-
-		const uri1 = TestWorkspace.folders[0].uri.with({ path: TestWorkspace.folders[0].uri.path.concat('/a/b/c/d') });
-		assert.equal(labelService.getUriLabel(uri1, { relative: true }), isWindows ? 'a\\b\\c\\d' : 'a/b/c/d');
-		assert.equal(labelService.getUriLabel(uri1, { relative: false }), isWindows ? 'C:\\testWorkspace\\a\\b\\c\\d' : '/testWorkspace/a/b/c/d');
-		assert.equal(labelService.getUriBasenameLabel(uri1), 'd');
-
-		const uri2 = URI.file('c:\\1/2/3');
-		assert.equal(labelService.getUriLabel(uri2, { relative: false }), isWindows ? 'C:\\1\\2\\3' : '/c:\\1/2/3');
-		assert.equal(labelService.getUriBasenameLabel(uri2), '3');
+		labelService = new LabelService(TestEnvironmentService, new TestContextService(), new TestRemotePathService());
 	});
 
 	test('custom scheme', function () {
diff --git a/src/vs/workbench/services/label/test/electron-browser/label.test.ts b/src/vs/workbench/services/label/test/electron-browser/label.test.ts
new file mode 100644
index 00000000000..ceb122d22a3
--- /dev/null
+++ b/src/vs/workbench/services/label/test/electron-browser/label.test.ts
@@ -0,0 +1,43 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as assert from 'assert';
+import { TestWorkspace } from 'vs/platform/workspace/test/common/testWorkspace';
+import { URI } from 'vs/base/common/uri';
+import { sep } from 'vs/base/common/path';
+import { isWindows } from 'vs/base/common/platform';
+import { LabelService } from 'vs/workbench/services/label/common/labelService';
+import { TestContextService } from 'vs/workbench/test/common/workbenchTestServices';
+import { TestNativeRemotePathService, TestEnvironmentService } from 'vs/workbench/test/electron-browser/workbenchTestServices';
+
+suite('URI Label', () => {
+
+	let labelService: LabelService;
+
+	setup(() => {
+		labelService = new LabelService(TestEnvironmentService, new TestContextService(), new TestNativeRemotePathService(TestEnvironmentService));
+	});
+
+	test('file scheme', function () {
+		labelService.registerFormatter({
+			scheme: 'file',
+			formatting: {
+				label: '${path}',
+				separator: sep,
+				tildify: !isWindows,
+				normalizeDriveLetter: isWindows
+			}
+		});
+
+		const uri1 = TestWorkspace.folders[0].uri.with({ path: TestWorkspace.folders[0].uri.path.concat('/a/b/c/d') });
+		assert.equal(labelService.getUriLabel(uri1, { relative: true }), isWindows ? 'a\\b\\c\\d' : 'a/b/c/d');
+		assert.equal(labelService.getUriLabel(uri1, { relative: false }), isWindows ? 'C:\\testWorkspace\\a\\b\\c\\d' : '/testWorkspace/a/b/c/d');
+		assert.equal(labelService.getUriBasenameLabel(uri1), 'd');
+
+		const uri2 = URI.file('c:\\1/2/3');
+		assert.equal(labelService.getUriLabel(uri2, { relative: false }), isWindows ? 'C:\\1\\2\\3' : '/c:\\1/2/3');
+		assert.equal(labelService.getUriBasenameLabel(uri2), '3');
+	});
+});
diff --git a/src/vs/workbench/services/path/browser/remotePathService.ts b/src/vs/workbench/services/path/browser/remotePathService.ts
new file mode 100644
index 00000000000..7aeaab0fe7f
--- /dev/null
+++ b/src/vs/workbench/services/path/browser/remotePathService.ts
@@ -0,0 +1,29 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { registerSingleton } from 'vs/platform/instantiation/common/extensions';
+import { IRemoteAgentService } from 'vs/workbench/services/remote/common/remoteAgentService';
+import { IRemotePathService, AbstractRemotePathService } from 'vs/workbench/services/path/common/remotePathService';
+import { IHistoryService } from 'vs/workbench/services/history/common/history';
+import { URI } from 'vs/base/common/uri';
+import { Schemas } from 'vs/base/common/network';
+import { IWorkbenchEnvironmentService } from 'vs/workbench/services/environment/common/environmentService';
+
+export class BrowserRemotePathService extends AbstractRemotePathService {
+
+	private static fallbackUserHome(historyService: IHistoryService, environmentService: IWorkbenchEnvironmentService): URI {
+		return historyService.getLastActiveWorkspaceRoot() || URI.from({ scheme: Schemas.vscodeRemote, authority: environmentService.configuration.remoteAuthority, path: '/' });
+	}
+
+	constructor(
+		@IRemoteAgentService remoteAgentService: IRemoteAgentService,
+		@IHistoryService historyService: IHistoryService,
+		@IWorkbenchEnvironmentService environmentService: IWorkbenchEnvironmentService
+	) {
+		super(() => BrowserRemotePathService.fallbackUserHome(historyService, environmentService), remoteAgentService);
+	}
+}
+
+registerSingleton(IRemotePathService, BrowserRemotePathService, true);
diff --git a/src/vs/workbench/services/path/common/remotePathService.ts b/src/vs/workbench/services/path/common/remotePathService.ts
index a1e875a0e13..94ea045d7e1 100644
--- a/src/vs/workbench/services/path/common/remotePathService.ts
+++ b/src/vs/workbench/services/path/common/remotePathService.ts
@@ -3,13 +3,11 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import * as path from 'vs/base/common/path';
-import * as platform from 'vs/base/common/platform';
+import { IPath, win32, posix } from 'vs/base/common/path';
+import { OperatingSystem, OS } from 'vs/base/common/platform';
 import { URI } from 'vs/base/common/uri';
-import { registerSingleton } from 'vs/platform/instantiation/common/extensions';
 import { createDecorator } from 'vs/platform/instantiation/common/instantiation';
 import { IRemoteAgentService } from 'vs/workbench/services/remote/common/remoteAgentService';
-import { IWorkbenchEnvironmentService } from 'vs/workbench/services/environment/common/environmentService';
 
 const REMOTE_PATH_SERVICE_ID = 'remotePath';
 export const IRemotePathService = createDecorator<IRemotePathService>(REMOTE_PATH_SERVICE_ID);
@@ -21,7 +19,7 @@ export interface IRemotePathService {
 	/**
 	 * The path library to use for the target remote environment.
 	 */
-	readonly path: Promise<path.IPath>;
+	readonly path: Promise<IPath>;
 
 	/**
 	 * Converts the given path to a file URI in the remote environment.
@@ -35,36 +33,50 @@ export interface IRemotePathService {
 
 	/**
 	 * Provides access to the user home of the remote environment
-	 * if defined.
+	 * if defined. The variable will be `undefined` as long as the
+	 * remote environment has not been resolved yet.
 	 */
-	readonly userHomeSync: URI | undefined;
+	readonly resolvedUserHome: URI | undefined;
 }
 
 /**
  * Provides the correct IPath implementation for dealing with paths that refer to locations in the extension host
  */
-export class RemotePathService implements IRemotePathService {
+export abstract class AbstractRemotePathService implements IRemotePathService {
+
 	_serviceBrand: undefined;
 
-	private _extHostOS: Promise<platform.OperatingSystem>;
-	private _userHomeSync: URI | undefined;
+	private remoteOS: Promise<OperatingSystem>;
+
+	private resolveUserHome: Promise<URI>;
+	private maybeUnresolvedUserHome: URI | undefined;
 
 	constructor(
-		@IRemoteAgentService private readonly remoteAgentService: IRemoteAgentService,
-		@IWorkbenchEnvironmentService private readonly environmentService: IWorkbenchEnvironmentService
+		fallbackUserHome: () => URI,
+		@IRemoteAgentService private readonly remoteAgentService: IRemoteAgentService
 	) {
-		this._extHostOS = remoteAgentService.getEnvironment().then(remoteEnvironment => {
-			this._userHomeSync = remoteEnvironment?.userHome;
+		this.remoteOS = this.remoteAgentService.getEnvironment().then(env => env?.os || OS);
 
-			return remoteEnvironment ? remoteEnvironment.os : platform.OS;
+		this.resolveUserHome = this.remoteAgentService.getEnvironment().then(env => {
+			const userHome = this.maybeUnresolvedUserHome = env?.userHome || fallbackUserHome();
+
+			return userHome;
 		});
 	}
 
-	get path(): Promise<path.IPath> {
-		return this._extHostOS.then(os => {
-			return os === platform.OperatingSystem.Windows ?
-				path.win32 :
-				path.posix;
+	get userHome(): Promise<URI> {
+		return this.resolveUserHome;
+	}
+
+	get resolvedUserHome(): URI | undefined {
+		return this.maybeUnresolvedUserHome;
+	}
+
+	get path(): Promise<IPath> {
+		return this.remoteOS.then(os => {
+			return os === OperatingSystem.Windows ?
+				win32 :
+				posix;
 		});
 	}
 
@@ -74,7 +86,7 @@ export class RemotePathService implements IRemotePathService {
 		// normalize to fwd-slashes on windows,
 		// on other systems bwd-slashes are valid
 		// filename character, eg /f\oo/ba\r.txt
-		if ((await this._extHostOS) === platform.OperatingSystem.Windows) {
+		if ((await this.remoteOS) === OperatingSystem.Windows) {
 			_path = _path.replace(/\\/g, '/');
 		}
 
@@ -100,23 +112,4 @@ export class RemotePathService implements IRemotePathService {
 			fragment: ''
 		});
 	}
-
-	get userHome(): Promise<URI> {
-		return this.remoteAgentService.getEnvironment().then(env => {
-
-			// remote: use remote environment userHome
-			if (env) {
-				return env.userHome;
-			}
-
-			// local: use the userHome from environment
-			return this.environmentService.userHome!;
-		});
-	}
-
-	get userHomeSync(): URI | undefined {
-		return this._userHomeSync || this.environmentService.userHome;
-	}
 }
-
-registerSingleton(IRemotePathService, RemotePathService, true);
diff --git a/src/vs/workbench/services/path/electron-browser/remotePathService.ts b/src/vs/workbench/services/path/electron-browser/remotePathService.ts
new file mode 100644
index 00000000000..67c74c0b0c9
--- /dev/null
+++ b/src/vs/workbench/services/path/electron-browser/remotePathService.ts
@@ -0,0 +1,22 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { registerSingleton } from 'vs/platform/instantiation/common/extensions';
+import { IRemoteAgentService } from 'vs/workbench/services/remote/common/remoteAgentService';
+import { IWorkbenchEnvironmentService } from 'vs/workbench/services/environment/common/environmentService';
+import { IRemotePathService, AbstractRemotePathService } from 'vs/workbench/services/path/common/remotePathService';
+import { INativeWorkbenchEnvironmentService } from 'vs/workbench/services/environment/electron-browser/environmentService';
+
+export class NativeRemotePathService extends AbstractRemotePathService {
+
+	constructor(
+		@IRemoteAgentService remoteAgentService: IRemoteAgentService,
+		@IWorkbenchEnvironmentService environmentService: INativeWorkbenchEnvironmentService
+	) {
+		super(() => environmentService.userHome, remoteAgentService);
+	}
+}
+
+registerSingleton(IRemotePathService, NativeRemotePathService, true);
diff --git a/src/vs/workbench/test/browser/workbenchTestServices.ts b/src/vs/workbench/test/browser/workbenchTestServices.ts
index 496550a2491..63f207772b1 100644
--- a/src/vs/workbench/test/browser/workbenchTestServices.ts
+++ b/src/vs/workbench/test/browser/workbenchTestServices.ts
@@ -115,7 +115,10 @@ export interface ITestInstantiationService extends IInstantiationService {
 	stub<T>(service: ServiceIdentifier<T>, ctor: any): T;
 }
 
-export function workbenchInstantiationService(overrides?: { textFileService?: (instantiationService: IInstantiationService) => ITextFileService }): ITestInstantiationService {
+export function workbenchInstantiationService(overrides?: {
+	textFileService?: (instantiationService: IInstantiationService) => ITextFileService
+	remotePathService?: (instantiationService: IInstantiationService) => IRemotePathService
+}): ITestInstantiationService {
 	const instantiationService = new TestInstantiationService(new ServiceCollection([ILifecycleService, new TestLifecycleService()]));
 
 	instantiationService.stub(IWorkingCopyService, new TestWorkingCopyService());
@@ -131,7 +134,7 @@ export function workbenchInstantiationService(overrides?: { textFileService?: (i
 	instantiationService.stub(ITextResourceConfigurationService, new TestTextResourceConfigurationService(configService));
 	instantiationService.stub(IUntitledTextEditorService, instantiationService.createInstance(UntitledTextEditorService));
 	instantiationService.stub(IStorageService, new TestStorageService());
-	instantiationService.stub(IRemotePathService, new TestRemotePathService(TestEnvironmentService));
+	instantiationService.stub(IRemotePathService, overrides?.remotePathService ? overrides.remotePathService(instantiationService) : new TestRemotePathService());
 	const layoutService = new TestLayoutService();
 	instantiationService.stub(IWorkbenchLayoutService, layoutService);
 	instantiationService.stub(IDialogService, new TestDialogService());
@@ -1108,12 +1111,12 @@ export class TestRemotePathService implements IRemotePathService {
 
 	_serviceBrand: undefined;
 
-	constructor(@IWorkbenchEnvironmentService private readonly environmentService: IEnvironmentService) { }
+	constructor(private readonly fallbackUserHome: URI = URI.from({ scheme: Schemas.vscodeRemote, path: '/' })) { }
 
 	get path() { return Promise.resolve(isWindows ? win32 : posix); }
 
-	get userHome() { return Promise.resolve(this.environmentService.userHome!); }
-	get userHomeSync() { return this.environmentService.userHome; }
+	get userHome() { return Promise.resolve(this.fallbackUserHome); }
+	get resolvedUserHome() { return this.fallbackUserHome; }
 
 	async fileURI(path: string): Promise<URI> {
 		return URI.file(path);
diff --git a/src/vs/workbench/test/electron-browser/workbenchTestServices.ts b/src/vs/workbench/test/electron-browser/workbenchTestServices.ts
index 13920be7069..fd17d5c30e3 100644
--- a/src/vs/workbench/test/electron-browser/workbenchTestServices.ts
+++ b/src/vs/workbench/test/electron-browser/workbenchTestServices.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { workbenchInstantiationService as browserWorkbenchInstantiationService, ITestInstantiationService, TestLifecycleService, TestFilesConfigurationService, TestFileService, TestFileDialogService } from 'vs/workbench/test/browser/workbenchTestServices';
+import { workbenchInstantiationService as browserWorkbenchInstantiationService, ITestInstantiationService, TestLifecycleService, TestFilesConfigurationService, TestFileService, TestFileDialogService, TestRemotePathService } from 'vs/workbench/test/browser/workbenchTestServices';
 import { Event } from 'vs/base/common/event';
 import { ISharedProcessService } from 'vs/platform/ipc/electron-browser/sharedProcessService';
 import { NativeWorkbenchEnvironmentService, INativeWorkbenchEnvironmentService } from 'vs/workbench/services/environment/electron-browser/environmentService';
@@ -219,7 +219,8 @@ export class TestElectronService implements IElectronService {
 
 export function workbenchInstantiationService(): ITestInstantiationService {
 	const instantiationService = browserWorkbenchInstantiationService({
-		textFileService: insta => <ITextFileService>insta.createInstance(TestTextFileService)
+		textFileService: insta => <ITextFileService>insta.createInstance(TestTextFileService),
+		remotePathService: insta => <IRemotePathService>insta.createInstance(TestNativeRemotePathService)
 	});
 
 	instantiationService.stub(IElectronService, new TestElectronService());
@@ -243,3 +244,12 @@ export class TestServiceAccessor {
 	) {
 	}
 }
+
+export class TestNativeRemotePathService extends TestRemotePathService {
+
+	_serviceBrand: undefined;
+
+	constructor(@IWorkbenchEnvironmentService environmentService: INativeWorkbenchEnvironmentService) {
+		super(environmentService.userHome);
+	}
+}
diff --git a/src/vs/workbench/workbench.common.main.ts b/src/vs/workbench/workbench.common.main.ts
index 7288803da97..d8ffd1576f2 100644
--- a/src/vs/workbench/workbench.common.main.ts
+++ b/src/vs/workbench/workbench.common.main.ts
@@ -76,7 +76,6 @@ import 'vs/workbench/services/extensionManagement/common/extensionEnablementServ
 import 'vs/workbench/services/notification/common/notificationService';
 import 'vs/workbench/services/extensions/common/staticExtensions';
 import 'vs/workbench/services/userDataSync/common/userDataSyncUtil';
-import 'vs/workbench/services/path/common/remotePathService';
 import 'vs/workbench/services/remote/common/remoteExplorerService';
 import 'vs/workbench/services/workingCopy/common/workingCopyService';
 import 'vs/workbench/services/workingCopy/common/workingCopyFileService';
diff --git a/src/vs/workbench/workbench.desktop.main.ts b/src/vs/workbench/workbench.desktop.main.ts
index cdd9d93c1ea..71fa3df99bc 100644
--- a/src/vs/workbench/workbench.desktop.main.ts
+++ b/src/vs/workbench/workbench.desktop.main.ts
@@ -66,6 +66,7 @@ import 'vs/workbench/services/update/electron-browser/updateService';
 import 'vs/workbench/services/issue/electron-browser/issueService';
 import 'vs/workbench/services/menubar/electron-browser/menubarService';
 import 'vs/workbench/services/extensionResourceLoader/electron-browser/extensionResourceLoaderService';
+import 'vs/workbench/services/path/electron-browser/remotePathService';
 
 import { registerSingleton } from 'vs/platform/instantiation/common/extensions';
 import { ICredentialsService } from 'vs/platform/credentials/common/credentials';
diff --git a/src/vs/workbench/workbench.web.main.ts b/src/vs/workbench/workbench.web.main.ts
index 82e9da5652f..ced463bc91e 100644
--- a/src/vs/workbench/workbench.web.main.ts
+++ b/src/vs/workbench/workbench.web.main.ts
@@ -50,6 +50,7 @@ import 'vs/workbench/services/request/browser/requestService';
 import 'vs/workbench/services/lifecycle/browser/lifecycleService';
 import 'vs/workbench/services/clipboard/browser/clipboardService';
 import 'vs/workbench/services/extensionResourceLoader/browser/extensionResourceLoaderService';
+import 'vs/workbench/services/path/browser/remotePathService';
 
 import { registerSingleton } from 'vs/platform/instantiation/common/extensions';
 import { IAccessibilityService } from 'vs/platform/accessibility/common/accessibility';