diff --git a/apps/web/next.config.ts b/apps/web/next.config.ts
index 73b55eb84..768b77fae 100644
--- a/apps/web/next.config.ts
+++ b/apps/web/next.config.ts
@@ -391,10 +391,12 @@ const nextConfig: NextConfig = {
           source: "/:path*\\.md",
           destination: "/api/markdown/:path*",
         },
-        // Markdown content negotiation for AI tools
+        // Markdown content negotiation for AI tools. beforeFiles rewrites
+        // chain, so skip paths the .md rule above already rewrote — otherwise
+        // /pricing.md + Accept: text/markdown ends up at /api/markdown/api/markdown/pricing
         {
-          source: "/:path*",
-          destination: "/api/markdown/:path*",
+          source: "/:path((?!api/markdown(?:/|$)).+)",
+          destination: "/api/markdown/:path",
           has: [
             {
               type: "header",