diff --git a/asteroid.lisp b/asteroid.lisp
index cbddc52..f125733 100644
--- a/asteroid.lisp
+++ b/asteroid.lisp
@@ -977,8 +977,11 @@
     
     ;; Serve regular static file
     (t
-     (serve-file (merge-pathnames (format nil "static/~a" path) 
-                                  (asdf:system-source-directory :asteroid))))))
+     (let ((file-path (merge-pathnames (format nil "static/~a" path)
+                                       (asdf:system-source-directory :asteroid))))
+       (if (probe-file file-path)
+           (serve-file file-path)
+           (error 'radiance:request-not-found))))))
 
 ;; Status check functions
 (defun check-icecast-status ()
@@ -1435,14 +1438,30 @@
 ;; RADIANCE server management functions
 
 (defun start-server (&key (port *server-port*))
-  "Start the Asteroid Radio RADIANCE server"
+  "Start the Asteroid Radio RADIANCE server.
+   Reads ASTEROID_DEBUG from the environment to control Radiance's debugger policy:
+     nil (or unset)       - never invoke debugger (production default)
+     if-swank-connected   - invoke only when Swank/Slynk is connected
+     t                    - always invoke debugger"
   (format t "Starting Asteroid Radio RADIANCE server on port ~a~%"  port)
   (compile-styles)  ; Generate CSS file using LASS
-  
-  ;; Ensure RADIANCE environment is properly set before startup
-  ;; (unless (radiance:environment)
-  ;;   (setf (radiance:environment) "asteroid"))
-  
+
+  ;; Set debugger policy from environment to prevent stray conditions from
+  ;; accumulating debugger sessions (e.g. vulnerability scanners hitting bogus paths)
+  (let ((debug-env (uiop:getenv "ASTEROID_DEBUG")))
+    (setf radiance:*debugger*
+          (cond
+            ((or (null debug-env)
+                 (string-equal debug-env "nil")
+                 (string-equal debug-env ""))
+             nil)
+            ((string-equal debug-env "t")
+             t)
+            ((string-equal debug-env "if-swank-connected")
+             :if-swank-connected)
+            (t nil)))
+    (format t "Debugger policy: ~a~%" radiance:*debugger*))
+
   (radiance:startup)
   
   ;; Start listener statistics polling
diff --git a/conditions.lisp b/conditions.lisp
index 7c1f38e..71e6d71 100644
--- a/conditions.lisp
+++ b/conditions.lisp
@@ -202,3 +202,27 @@
   (error 'authorization-error
          :message message
          :required-role required-role))
+
+;;; Override Radiance's default render-error-page to return proper HTTP
+;;; status codes instead of a blanket 500 for conditions like
+;;; request-not-found and file-to-serve-does-not-exist. This prevents
+;;; vulnerability scanners from generating misleading 500 responses and
+;;; gives us control over error presentation.
+(defun radiance:render-error-page (condition)
+  (cond
+    ((typep condition 'radiance:request-not-found)
+     (setf (radiance:return-code radiance:*response*) 404)
+     (setf (radiance:content-type radiance:*response*) "text/plain")
+     "Not Found")
+    ((typep condition 'radiance:file-to-serve-does-not-exist)
+     (setf (radiance:return-code radiance:*response*) 404)
+     (setf (radiance:content-type radiance:*response*) "text/plain")
+     "Not Found")
+    ((typep condition 'radiance:request-denied)
+     (setf (radiance:return-code radiance:*response*) 403)
+     (setf (radiance:content-type radiance:*response*) "text/plain")
+     "Forbidden")
+    (t
+     (setf (radiance:return-code radiance:*response*) 500)
+     (setf (radiance:content-type radiance:*response*) "text/plain")
+     "Internal Server Error")))