diff --git a/vite.config.ts b/vite.config.ts
index 49683b9e9..6e618e172 100644
--- a/vite.config.ts
+++ b/vite.config.ts
@@ -1,8 +1,46 @@
 import tailwindcss from "@tailwindcss/vite";
 import press from "fumapress/vite";
 import { fumadocsMdx } from "fumadocs-mdx/vite";
-import { defineConfig } from "vite";
+import { defineConfig, type Plugin } from "vite";
+
+/**
+ * Mirror the base-path prefixing that the production build applies.
+ *
+ * `npm run build` finishes with `scripts/finalize-base-path.mjs`, which rewrites
+ * root-absolute asset URLs in the generated output so they resolve under the
+ * docs mount point inside langbot-landing-page (https://langbot.app/docs/...).
+ *
+ * The dev server serves the same content under `basePath: "/docs/"` but never
+ * runs that step, so those URLs 404 locally. Only assets that survive as literal
+ * root-absolute strings are affected: icons referenced from `docs.json` and the
+ * brand logo in `press.config.tsx`. Markdown images are unaffected because the
+ * asset pipeline rewrites them itself.
+ *
+ * The rule set intentionally mirrors `scripts/finalize-base-path.mjs` exactly, so
+ * a URL that is broken locally is broken in production too, and vice versa.
+ */
+const prefixBasePathAssets = (): Plugin => ({
+  name: "docs-dev-base-path-assets",
+  apply: "serve",
+  configureServer(server) {
+    server.middlewares.use((req, _res, next) => {
+      const url = req.url ?? "";
+      const isUnprefixedAsset =
+        url.startsWith("/images/") ||
+        url.startsWith("/favicon.ico") ||
+        url.startsWith("/langbot-logo.png") ||
+        url.startsWith("/rss.xml");
+      if (isUnprefixedAsset) req.url = `/docs${url}`;
+      next();
+    });
+  },
+});
 
 export default defineConfig({
-  plugins: [press({ basePath: "/docs/" }), fumadocsMdx(), tailwindcss()],
+  plugins: [
+    prefixBasePathAssets(),
+    press({ basePath: "/docs/" }),
+    fumadocsMdx(),
+    tailwindcss(),
+  ],
 });