diff --git a/src/browser/app.tsx b/src/browser/app.tsx
index dd0a6e251..16f639ed2 100644
--- a/src/browser/app.tsx
+++ b/src/browser/app.tsx
@@ -1,3 +1,4 @@
+import { field, logger } from "@coder/logger"
 import { getBasepath, navigate, setBasepath } from "hookrouter"
 import * as React from "react"
 import { Application, isExecutableApplication } from "../common/api"
@@ -14,16 +15,25 @@ interface RedirectedApplication extends Application {
   redirected?: boolean
 }
 
-const origin = typeof window !== "undefined" ? window.location.origin + window.location.pathname : undefined
-
+let resolved = false
 const App: React.FunctionComponent<AppProps> = (props) => {
   const [authed, setAuthed] = React.useState<boolean>(props.options.authed)
   const [app, setApp] = React.useState<RedirectedApplication | undefined>(props.options.app)
   const [error, setError] = React.useState<HttpError | Error | string>()
 
-  if (typeof window !== "undefined") {
-    const url = new URL(origin + props.options.basePath)
+  if (!resolved && typeof document !== "undefined") {
+    // Get the base path. We need the full URL for connecting the web socket.
+    // Use the path name plus the provided base path. For example:
+    // foo.com/base + ./ => foo.com/base
+    // foo.com/base/ + ./ => foo.com/base
+    // foo.com/base/bar + ./ => foo.com/base
+    // foo.com/base/bar/ + ./../ => foo.com/base
+    const parts = window.location.pathname.replace(/^\//g, "").split("/")
+    parts[parts.length - 1] = props.options.basePath
+    const url = new URL(window.location.origin + "/" + parts.join("/"))
     setBasepath(normalize(url.pathname))
+    logger.debug("resolved base path", field("base", getBasepath()))
+    resolved = true
 
     // eslint-disable-next-line @typescript-eslint/no-explicit-any
     ;(window as any).setAuthed = (a: boolean): void => {
diff --git a/src/node/http.ts b/src/node/http.ts
index 7c023956c..5c2989e18 100644
--- a/src/node/http.ts
+++ b/src/node/http.ts
@@ -117,8 +117,9 @@ interface ProviderRoute extends Route {
 
 export interface HttpProviderOptions {
   readonly auth: AuthType
-  readonly password?: string
+  readonly base: string
   readonly commit: string
+  readonly password?: string
 }
 
 /**
@@ -150,10 +151,16 @@ export abstract class HttpProvider {
   public abstract handleRequest(route: Route, request: http.IncomingMessage): Promise<HttpResponse | undefined>
 
   /**
-   * Get the base relative to the provided route.
+   * Get the base relative to the provided route. For each slash we need to go
+   * up a directory. For example:
+   * / => ./
+   * /foo => ./
+   * /foo/ => ./../
+   * /foo/bar => ./../
+   * /foo/bar/ => ./../../
    */
   public base(route: Route): string {
-    const depth = ((route.fullPath + "/").match(/\//g) || []).length
+    const depth = (route.originalPath.match(/\//g) || []).length
     return normalize("./" + (depth > 1 ? "../".repeat(depth - 1) : ""))
   }
 
@@ -403,6 +410,7 @@ export class HttpServer {
       new provider(
         {
           auth: this.options.auth || AuthType.None,
+          base: `/${endpoint}`,
           commit: this.options.commit,
           password: this.options.password,
         },
@@ -510,11 +518,6 @@ export class HttpServer {
       return { redirect: redirect(route.fullPath) }
     }
 
-    // Redirect our indexes to a trailing slash so relative paths in the served
-    // HTML will operate against the base path properly.
-    if (route.requestPath === "/index.html" && !route.originalPath.endsWith("/") && this.providers.has(route.base)) {
-      return { redirect: redirect(route.fullPath + "/") }
-    }
     return undefined
   }
 
@@ -572,7 +575,7 @@ export class HttpServer {
     }
 
     const parsedUrl = request.url ? url.parse(request.url, true) : { query: {}, pathname: "" }
-    const originalPath = parsedUrl.pathname || ""
+    const originalPath = parsedUrl.pathname || "/"
     const fullPath = normalize(originalPath)
     const { base, requestPath } = parse(fullPath)
 
diff --git a/src/node/vscode/server.ts b/src/node/vscode/server.ts
index acbf25eb3..6d26188b8 100644
--- a/src/node/vscode/server.ts
+++ b/src/node/vscode/server.ts
@@ -199,6 +199,8 @@ export class VscodeHttpProvider extends HttpProvider {
       ...response,
       content: response.content
         .replace(/{{COMMIT}}/g, options.commit)
+        .replace(/{{BASE}}/g, this.base(route))
+        .replace(/{{VS_BASE}}/g, this.base(route) + this.options.base)
         .replace(`"{{REMOTE_USER_DATA_URI}}"`, `'${JSON.stringify(options.remoteUserDataUri)}'`)
         .replace(`"{{PRODUCT_CONFIGURATION}}"`, `'${JSON.stringify(options.productConfiguration)}'`)
         .replace(`"{{WORKBENCH_WEB_CONFIGURATION}}"`, `'${JSON.stringify(options.workbenchWebConfiguration)}'`)
diff --git a/src/node/vscode/workbench-build.html b/src/node/vscode/workbench-build.html
index 6a417ce8c..86c0de0ff 100644
--- a/src/node/vscode/workbench-build.html
+++ b/src/node/vscode/workbench-build.html
@@ -19,28 +19,27 @@
     <meta id="vscode-remote-nls-configuration" data-settings="{{NLS_CONFIGURATION}}">
 
     <!-- Workbench Icon/Manifest/CSS -->
-    <link rel="icon" href="../static-{{COMMIT}}/src/browser/media/favicon.ico" type="image/x-icon" />
-    <link rel="manifest" href="../static-{{COMMIT}}/src/browser/media/manifest.json" crossorigin="use-credentials">
-    <link data-name="vs/workbench/workbench.web.api" rel="stylesheet" href="./static-{{COMMIT}}/out/vs/workbench/workbench.web.api.css">
-    <link rel="apple-touch-icon" href="../static-{{COMMIT}}/src/browser/media/code-server.png" />
+    <link rel="icon" href="{{BASE}}/static-{{COMMIT}}/src/browser/media/favicon.ico" type="image/x-icon" />
+    <link rel="manifest" href="{{BASE}}/static-{{COMMIT}}/src/browser/media/manifest.json" crossorigin="use-credentials">
+    <link data-name="vs/workbench/workbench.web.api" rel="stylesheet" href="{{VS_BASE}}/static-{{COMMIT}}/out/vs/workbench/workbench.web.api.css">
+    <link rel="apple-touch-icon" href="{{BASE}}/static-{{COMMIT}}/src/browser/media/code-server.png" />
     <meta name="apple-mobile-web-app-capable" content="yes">
 
     <!-- Prefetch to avoid waterfall -->
-    <link rel="prefetch" href="./static-{{COMMIT}}/node_modules/semver-umd/lib/semver-umd.js">
+    <link rel="prefetch" href="{{BASE}}/static-{{COMMIT}}/node_modules/semver-umd/lib/semver-umd.js">
   </head>
 
   <body aria-label="">
   </body>
 
   <!-- Startup (do not modify order of script tags!) -->
-  <!-- NOTE:coder: Modified to work against the current path and use the commit for caching. -->
   <script>
-    // NOTE: Changes to inline scripts require update of content security policy
-    const basePath = window.location.pathname.replace(/\/+$/, '');
-    const base = window.location.origin  + basePath;
+    const parts = window.location.pathname.replace(/^\//g, "").split("/")
+    parts[parts.length - 1] = "{{VS_BASE}}"
+    const url = new URL(window.location.origin + "/" + parts.join("/"))
     const el = document.getElementById('vscode-remote-commit');
     const commit = el ? el.getAttribute('data-settings') : "";
-    const staticBase = base + '/static-' + commit;
+    const staticBase = url.href + '/static-' + commit;
     let nlsConfig;
     try {
         nlsConfig = JSON.parse(document.getElementById('vscode-remote-nls-configuration').getAttribute('data-settings'));
@@ -54,7 +53,7 @@
                 // FIXME: Only works if path separators are /.
                 const path = nlsConfig._resolvedLanguagePackCoreLocation
                       + '/' + bundle.replace(/\//g, '!') + '.nls.json';
-                fetch(`${base}/resource/?path=${encodeURIComponent(path)}`)
+                fetch(`${url.href}/resource/?path=${encodeURIComponent(path)}`)
                     .then((response) => response.json())
                     .then((json) => {
                         bundles[bundle] = json;
@@ -78,15 +77,14 @@
         'vs/nls': nlsConfig,
     };
   </script>
-  <script src="./static-{{COMMIT}}/out/vs/loader.js"></script>
-  <script src="./static-{{COMMIT}}/out/vs/workbench/workbench.web.api.nls.js"></script>
-  <script src="./static-{{COMMIT}}/out/vs/workbench/workbench.web.api.js"></script>
+  <script src="{{VS_BASE}}/static-{{COMMIT}}/out/vs/loader.js"></script>
+  <script src="{{VS_BASE}}/static-{{COMMIT}}/out/vs/workbench/workbench.web.api.nls.js"></script>
+  <script src="{{VS_BASE}}/static-{{COMMIT}}/out/vs/workbench/workbench.web.api.js"></script>
   <!-- TODO@coder: This errors with multiple anonymous define calls (one is
        workbench.js and one is semver-umd.js). For now use the same method found in
        workbench-dev.html. Appears related to the timing of the script load events. -->
-  <!-- <script src="./static-{{COMMIT}}/out/vs/workbench/workbench.js"></script> -->
+  <!-- <script src="{{VS_BASE}}/static-{{COMMIT}}/out/vs/workbench/workbench.js"></script> -->
   <script>
-    // NOTE: Changes to inline scripts require update of content security policy
     require(['vs/code/browser/workbench/workbench'], function() {});
   </script>
 </html>
diff --git a/src/node/vscode/workbench.html b/src/node/vscode/workbench.html
index b7bb72b26..bb61eaf65 100644
--- a/src/node/vscode/workbench.html
+++ b/src/node/vscode/workbench.html
@@ -19,9 +19,9 @@
     <meta id="vscode-remote-nls-configuration" data-settings="{{NLS_CONFIGURATION}}">
 
     <!-- Workbench Icon/Manifest/CSS -->
-    <link rel="icon" href="../static/src/browser/media/favicon.ico" type="image/x-icon" />
-    <link rel="manifest" href="../static/src/browser/media/manifest.json" crossorigin="use-credentials">
-    <link rel="apple-touch-icon" href="../static/src/browser/media/code-server.png" />
+    <link rel="icon" href="{{BASE}}/static/src/browser/media/favicon.ico" type="image/x-icon" />
+    <link rel="manifest" href="{{BASE}}/static/src/browser/media/manifest.json" crossorigin="use-credentials">
+    <link rel="apple-touch-icon" href="{{BASE}}/static/src/browser/media/code-server.png" />
     <meta name="apple-mobile-web-app-capable" content="yes">
   </head>
 
@@ -30,11 +30,12 @@
 
   <!-- Startup (do not modify order of script tags!) -->
   <script>
-    const basePath = window.location.pathname.replace(/\/+$/, '');
-    const base = window.location.origin  + basePath;
+    const parts = window.location.pathname.replace(/^\//g, "").split("/")
+    parts[parts.length - 1] = "{{VS_BASE}}"
+    const url = new URL(window.location.origin + "/" + parts.join("/"))
     const el = document.getElementById('vscode-remote-commit');
     const commit = el ? el.getAttribute('data-settings') : "";
-    const staticBase = base + '/static-' + commit;
+    const staticBase = url.href + '/static-' + commit;
     self.require = {
         baseUrl: `${staticBase}/out`,
         paths: {
@@ -48,7 +49,7 @@
         },
     };
   </script>
-  <script src="./static/out/vs/loader.js"></script>
+  <script src="{{VS_BASE}}/static/out/vs/loader.js"></script>
   <script>
     require(['vs/code/browser/workbench/workbench'], function() {});
   </script>