diff --git a/internal/outpost/proxyv2/application/mode_forward.go b/internal/outpost/proxyv2/application/mode_forward.go
index 08b831d7d..7434c0ec6 100644
--- a/internal/outpost/proxyv2/application/mode_forward.go
+++ b/internal/outpost/proxyv2/application/mode_forward.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"net/http"
 	"net/url"
+	"strings"
 
 	"goauthentik.io/api"
 	"goauthentik.io/internal/outpost/proxyv2/constants"
@@ -34,6 +35,10 @@ func (a *Application) forwardHandleTraefik(rw http.ResponseWriter, r *http.Reque
 		a.log.Trace("path can be accessed without authentication")
 		return
 	}
+	if strings.HasPrefix(r.Header.Get("X-Forwarded-Uri"), "/akprox") {
+		a.log.WithField("url", r.URL.String()).Trace("path begins with /akprox, allowing access")
+		return
+	}
 	host := ""
 	s, _ := a.sessions.Get(r, constants.SeesionName)
 	// Optional suffix, which is appended to the URL
@@ -49,14 +54,6 @@ func (a *Application) forwardHandleTraefik(rw http.ResponseWriter, r *http.Reque
 	// see https://doc.traefik.io/traefik/middlewares/forwardauth/
 	// X-Forwarded-Uri is only the path, so we need to build the entire URL
 	s.Values[constants.SessionRedirect] = a.getTraefikForwardUrl(r).String()
-	if r.Header.Get("X-Forwarded-Uri") == "/akprox/start" {
-		a.log.Info("Detected potential redirect loop")
-		if val, ok := s.Values[constants.SessionLoopDetection]; !ok {
-			s.Values[constants.SessionLoopDetection] = 1
-		} else {
-			s.Values[constants.SessionLoopDetection] = val.(int) + 1
-		}
-	}
 	err = s.Save(r, rw)
 	if err != nil {
 		a.log.WithError(err).Warning("failed to save session before redirect")
@@ -83,5 +80,9 @@ func (a *Application) forwardHandleNginx(rw http.ResponseWriter, r *http.Request
 		a.log.Trace("path can be accessed without authentication")
 		return
 	}
+	if strings.HasPrefix(a.getTraefikForwardUrl(r).Path, "/akprox") {
+		a.log.WithField("url", r.URL.String()).Trace("path begins with /akprox, allowing access")
+		return
+	}
 	http.Error(rw, "unauthorized request", http.StatusUnauthorized)
 }
diff --git a/internal/outpost/proxyv2/application/oauth.go b/internal/outpost/proxyv2/application/oauth.go
index 6029a39ee..494c2f382 100644
--- a/internal/outpost/proxyv2/application/oauth.go
+++ b/internal/outpost/proxyv2/application/oauth.go
@@ -25,13 +25,6 @@ func (a *Application) handleRedirect(rw http.ResponseWriter, r *http.Request) {
 	if err != nil {
 		a.log.WithError(err).Warning("failed to save session")
 	}
-	if loop, ok := s.Values[constants.SessionLoopDetection]; ok {
-		if loop.(int) > 10 {
-			rw.WriteHeader(http.StatusBadRequest)
-			a.ErrorPage(rw, r, "Detected redirect loop, make sure /akprox is accessible without authentication.")
-			return
-		}
-	}
 	http.Redirect(rw, r, a.oauthConfig.AuthCodeURL(newState), http.StatusFound)
 }
 
diff --git a/internal/outpost/proxyv2/constants/constants.go b/internal/outpost/proxyv2/constants/constants.go
index bb7d790da..3160f42bd 100644
--- a/internal/outpost/proxyv2/constants/constants.go
+++ b/internal/outpost/proxyv2/constants/constants.go
@@ -6,4 +6,3 @@ const SessionOAuthState = "oauth_state"
 const SessionClaims = "claims"
 
 const SessionRedirect = "redirect"
-const SessionLoopDetection = "loop_detection"