diff --git a/zio-http/shared/src/main/scala/zio/http/Routes.scala b/zio-http/shared/src/main/scala/zio/http/Routes.scala
index 8695ebd2ea..2179bf9d8b 100644
--- a/zio-http/shared/src/main/scala/zio/http/Routes.scala
+++ b/zio-http/shared/src/main/scala/zio/http/Routes.scala
@@ -248,14 +248,18 @@ final case class Routes[-Env, +Err](routes: Chunk[zio.http.Route[Env, Err]]) { s
     val tree                  = self.tree
     Handler
       .fromFunctionHandler[Request] { req =>
+        println(s"[DEBUG] Incoming request: Method = ${req.method}, Path = ${req.path}")
+
         val chunk          = tree.get(req.method, req.path)
         def allowedMethods = tree.getAllMethods(req.path)
+        println(s"[DEBUG] Chunk length for Method ${req.method} and Path ${req.path} = ${chunk.length}")
+        println(s"[DEBUG] Allowed methods for Path ${req.path} = ${allowedMethods.mkString(", ")}")
         req.method match {
           case Method.CUSTOM(_) =>
             Handler.notImplemented
           case _                =>
             if (chunk.isEmpty) {
-              if (allowedMethods.isEmpty) {
+              if (allowedMethods.isEmpty || allowedMethods == Set(Method.OPTIONS)) {
                 // If no methods are allowed for the path, return 404 Not Found
                 Handler.notFound
               } else {
@@ -281,6 +285,7 @@ final case class Routes[-Env, +Err](routes: Chunk[zio.http.Route[Env, Err]]) { s
               }
             }
         }
+
       }
       .merge
   }