diff --git a/internal/web/web_static.go b/internal/web/web_static.go
index bac67c2b4..0780377bb 100644
--- a/internal/web/web_static.go
+++ b/internal/web/web_static.go
@@ -1,8 +1,10 @@
 package web
 
 import (
+	"fmt"
 	"net/http"
 
+	"github.com/gorilla/mux"
 	"goauthentik.io/internal/config"
 	"goauthentik.io/internal/constants"
 	staticWeb "goauthentik.io/web"
@@ -15,22 +17,32 @@ func (ws *WebServer) configureStatic() {
 	// Media files, always local
 	fs := http.FileServer(http.Dir(config.G.Paths.Media))
 	var distHandler http.Handler
+	var distFs http.Handler
 	var authentikHandler http.Handler
 	var helpHandler http.Handler
 	if config.G.Debug || config.G.Web.LoadLocalFiles {
 		ws.log.Debug("Using local static files")
-		distHandler = http.StripPrefix("/static/dist/", http.FileServer(http.Dir("./web/dist")))
+		distFs = http.FileServer(http.Dir("./web/dist"))
+		distHandler = http.StripPrefix("/static/dist/", distFs)
 		authentikHandler = http.StripPrefix("/static/authentik/", http.FileServer(http.Dir("./web/authentik")))
 		helpHandler = http.StripPrefix("/help/", http.FileServer(http.Dir("./website/help")))
 	} else {
 		statRouter.Use(ws.staticHeaderMiddleware)
 		ws.log.Debug("Using packaged static files with aggressive caching")
-		distHandler = http.StripPrefix("/static", http.FileServer(http.FS(staticWeb.StaticDist)))
+		distFs = http.FileServer(http.FS(staticWeb.StaticDist))
+		distHandler = http.StripPrefix("/static", distFs)
 		authentikHandler = http.StripPrefix("/static", http.FileServer(http.FS(staticWeb.StaticAuthentik)))
 		helpHandler = http.FileServer(http.FS(staticDocs.Help))
 	}
 	statRouter.PathPrefix("/static/dist/").Handler(distHandler)
 	statRouter.PathPrefix("/static/authentik/").Handler(authentikHandler)
+	// Prevent font-loading issues on safari, which loads fonts relatively to the URL the browser is on
+	statRouter.PathPrefix("/if/flow/{flow_slug}/assets").HandlerFunc(func(rw http.ResponseWriter, r *http.Request) {
+		vars := mux.Vars(r)
+
+		http.StripPrefix(fmt.Sprintf("/if/flow/%s", vars["flow_slug"]), distFs).ServeHTTP(rw, r)
+	})
+	statRouter.PathPrefix("/if/admin/assets").Handler(http.StripPrefix("/if/admin", distFs))
 
 	statRouter.PathPrefix("/media/").Handler(http.StripPrefix("/media", fs))