diff --git a/internal/web/web_static.go b/internal/web/web_static.go
index 06d30eddd..ccee1c98d 100644
--- a/internal/web/web_static.go
+++ b/internal/web/web_static.go
@@ -10,15 +10,19 @@ import (
 
 func (ws *WebServer) configureStatic() {
 	statRouter := ws.lh.NewRoute().Subrouter()
+	// Media files, always local
+	fs := http.FileServer(http.Dir(config.G.Paths.Media))
 	if config.G.Debug || config.G.Web.LoadLocalFiles {
 		ws.log.Debug("Using local static files")
-		ws.lh.PathPrefix("/static/dist").Handler(http.StripPrefix("/static/dist", http.FileServer(http.Dir("./web/dist"))))
-		ws.lh.PathPrefix("/static/authentik").Handler(http.StripPrefix("/static/authentik", http.FileServer(http.Dir("./web/authentik"))))
+		statRouter.PathPrefix("/static/dist").Handler(http.StripPrefix("/static/dist", http.FileServer(http.Dir("./web/dist"))))
+		statRouter.PathPrefix("/static/authentik").Handler(http.StripPrefix("/static/authentik", http.FileServer(http.Dir("./web/authentik"))))
+		statRouter.PathPrefix("/media").Handler(http.StripPrefix("/media", fs))
 	} else {
 		statRouter.Use(ws.staticHeaderMiddleware)
 		ws.log.Debug("Using packaged static files with aggressive caching")
-		ws.lh.PathPrefix("/static/dist").Handler(http.StripPrefix("/static", http.FileServer(http.FS(staticWeb.StaticDist))))
-		ws.lh.PathPrefix("/static/authentik").Handler(http.StripPrefix("/static", http.FileServer(http.FS(staticWeb.StaticAuthentik))))
+		statRouter.PathPrefix("/static/dist").Handler(http.StripPrefix("/static", http.FileServer(http.FS(staticWeb.StaticDist))))
+		statRouter.PathPrefix("/static/authentik").Handler(http.StripPrefix("/static", http.FileServer(http.FS(staticWeb.StaticAuthentik))))
+		statRouter.PathPrefix("/media").Handler(http.StripPrefix("/media", fs))
 	}
 	ws.lh.Path("/robots.txt").HandlerFunc(func(rw http.ResponseWriter, r *http.Request) {
 		rw.Header()["Content-Type"] = []string{"text/plain"}
@@ -30,8 +34,6 @@ func (ws *WebServer) configureStatic() {
 		rw.WriteHeader(200)
 		rw.Write(staticWeb.SecurityTxt)
 	})
-	// Media files, always local
-	ws.lh.PathPrefix("/media").Handler(http.StripPrefix("/media", http.FileServer(http.Dir(config.G.Paths.Media))))
 }
 
 func (ws *WebServer) staticHeaderMiddleware(h http.Handler) http.Handler {