diff --git a/src/vs/server/node/webClientServer.ts b/src/vs/server/node/webClientServer.ts
index b8d59486d7a..d6a590c590e 100644
--- a/src/vs/server/node/webClientServer.ts
+++ b/src/vs/server/node/webClientServer.ts
@@ -98,6 +98,7 @@ export class WebClientServer {
 
 	private readonly _staticRoute: string;
 	private readonly _callbackRoute: string;
+	private readonly _webExtensionRoute: string;
 
 	constructor(
 		private readonly _connectionToken: ServerConnectionToken,
@@ -110,6 +111,7 @@ export class WebClientServer {
 		const serverRootPath = getRemoteServerRootPath(_productService);
 		this._staticRoute = `${serverRootPath}/static`;
 		this._callbackRoute = `${serverRootPath}/callback`;
+		this._webExtensionRoute = `${serverRootPath}/web-extension-resource`;
 	}
 
 	/**
@@ -131,7 +133,7 @@ export class WebClientServer {
 				// callback support
 				return this._handleCallback(res);
 			}
-			if (/^\/web-extension-resource\//.test(pathname)) {
+			if (pathname.startsWith(this._webExtensionRoute) && pathname.charCodeAt(this._webExtensionRoute.length) === CharCode.Slash) {
 				// extension resource support
 				return this._handleWebExtensionResource(req, res, parsedUrl);
 			}
@@ -177,7 +179,7 @@ export class WebClientServer {
 
 		// Strip `/web-extension-resource/` from the path
 		const normalizedPathname = decodeURIComponent(parsedUrl.pathname!); // support paths that are uri-encoded (e.g. spaces => %20)
-		const path = normalize(normalizedPathname.substr('/web-extension-resource/'.length));
+		const path = normalize(normalizedPathname.substring(this._webExtensionRoute.length + 1));
 		const uri = URI.parse(path).with({
 			scheme: this._webExtensionResourceUrlTemplate.scheme,
 			authority: path.substring(0, path.indexOf('/')),
@@ -311,7 +313,7 @@ export class WebClientServer {
 					'resourceUrlTemplate': this._webExtensionResourceUrlTemplate.with({
 						scheme: 'http',
 						authority: remoteAuthority,
-						path: `web-extension-resource/${this._webExtensionResourceUrlTemplate.authority}${this._webExtensionResourceUrlTemplate.path}`
+						path: `${this._webExtensionRoute}/${this._webExtensionResourceUrlTemplate.authority}${this._webExtensionResourceUrlTemplate.path}`
 					}).toString(true)
 				} : undefined
 			},
diff --git a/src/vs/workbench/services/extensionResourceLoader/common/extensionResourceLoader.ts b/src/vs/workbench/services/extensionResourceLoader/common/extensionResourceLoader.ts
index a790241645c..6991120b691 100644
--- a/src/vs/workbench/services/extensionResourceLoader/common/extensionResourceLoader.ts
+++ b/src/vs/workbench/services/extensionResourceLoader/common/extensionResourceLoader.ts
@@ -17,6 +17,7 @@ import { IStorageService } from 'vs/platform/storage/common/storage';
 import { TelemetryLevel } from 'vs/platform/telemetry/common/telemetry';
 import { getTelemetryLevel, supportsTelemetry } from 'vs/platform/telemetry/common/telemetryUtils';
 import { RemoteAuthorities } from 'vs/base/common/network';
+import { getRemoteServerRootPath } from 'vs/platform/remote/common/remoteHosts';
 
 export const WEB_EXTENSION_RESOURCE_END_POINT = 'web-extension-resource';
 
@@ -49,6 +50,7 @@ export abstract class AbstractExtensionResourceLoaderService implements IExtensi
 
 	readonly _serviceBrand: undefined;
 
+	private readonly _webExtensionResourceEndPoint: string;
 	private readonly _extensionGalleryResourceUrlTemplate: string | undefined;
 	private readonly _extensionGalleryAuthority: string | undefined;
 
@@ -59,6 +61,7 @@ export abstract class AbstractExtensionResourceLoaderService implements IExtensi
 		private readonly _environmentService: IEnvironmentService,
 		private readonly _configurationService: IConfigurationService,
 	) {
+		this._webExtensionResourceEndPoint = `${getRemoteServerRootPath(_productService)}/${WEB_EXTENSION_RESOURCE_END_POINT}/`;
 		if (_productService.extensionsGallery) {
 			this._extensionGalleryResourceUrlTemplate = _productService.extensionsGallery.resourceUrlTemplate;
 			this._extensionGalleryAuthority = this._extensionGalleryResourceUrlTemplate ? this._getExtensionGalleryAuthority(URI.parse(this._extensionGalleryResourceUrlTemplate)) : undefined;
@@ -115,7 +118,7 @@ export abstract class AbstractExtensionResourceLoaderService implements IExtensi
 	}
 
 	protected _isWebExtensionResourceEndPoint(uri: URI): boolean {
-		return uri.path.startsWith(`/${WEB_EXTENSION_RESOURCE_END_POINT}/`);
+		return uri.path.startsWith(this._webExtensionResourceEndPoint);
 	}
 
 }