diff --git a/src/channel.ts b/src/channel.ts
index 9ce9e008a..99fcb384d 100644
--- a/src/channel.ts
+++ b/src/channel.ts
@@ -164,8 +164,8 @@ export class FileProviderChannel implements IServerChannel, IDisposable {
 
 	private transform(resource: UriComponents): URI {
 		// Used for walkthrough content.
-		if (resource.path.indexOf("/static") === 0) {
-			return URI.file(this.environmentService.appRoot + resource.path.replace(/^\/static/, ""));
+		if (/^\/static[^/]*\//.test(resource.path)) {
+			return URI.file(this.environmentService.appRoot + resource.path.replace(/^\/static[^/]*\//, "/"));
 		// Used by the webview service worker to load resources.
 		} else if (resource.path === "/vscode-resource" && resource.query) {
 			try {
diff --git a/src/server.ts b/src/server.ts
index 5cb8770c3..1fd57b9f0 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -279,7 +279,7 @@ export abstract class Server {
 		// without adding query parameters which have their own issues.
 		// REVIEW: Discuss whether this is the best option; this is sort of a quick
 		// hack almost to get caching in the meantime but it does work pretty well.
-		if (/static-.+/.test(base)) {
+		if (/^\/static-.+/.test(base)) {
 			base = "/static";
 		}