diff --git a/outpost/pkg/ak/api_ws.go b/outpost/pkg/ak/api_ws.go
index 851266aa9..235247ec1 100644
--- a/outpost/pkg/ak/api_ws.go
+++ b/outpost/pkg/ak/api_ws.go
@@ -15,9 +15,9 @@ import (
 	"goauthentik.io/outpost/pkg"
 )
 
-func (ac *APIController) initWS(pbURL url.URL, outpostUUID strfmt.UUID) {
+func (ac *APIController) initWS(akURL url.URL, outpostUUID strfmt.UUID) {
 	pathTemplate := "%s://%s/ws/outpost/%s/"
-	scheme := strings.ReplaceAll(pbURL.Scheme, "http", "ws")
+	scheme := strings.ReplaceAll(akURL.Scheme, "http", "ws")
 
 	authHeader := fmt.Sprintf("Bearer %s", ac.token)
 
@@ -37,7 +37,7 @@ func (ac *APIController) initWS(pbURL url.URL, outpostUUID strfmt.UUID) {
 			InsecureSkipVerify: strings.ToLower(value) == "true",
 		},
 	}
-	ws.Dial(fmt.Sprintf(pathTemplate, scheme, pbURL.Host, outpostUUID.String()), header)
+	ws.Dial(fmt.Sprintf(pathTemplate, scheme, akURL.Host, outpostUUID.String()), header)
 
 	ac.logger.WithField("logger", "authentik.outpost.ak-ws").WithField("outpost", outpostUUID.String()).Debug("connecting to authentik")
 
diff --git a/outpost/pkg/proxy/middleware.go b/outpost/pkg/proxy/middleware.go
index 3e9e924fc..7c938ea77 100644
--- a/outpost/pkg/proxy/middleware.go
+++ b/outpost/pkg/proxy/middleware.go
@@ -107,7 +107,7 @@ func (h loggingHandler) ServeHTTP(w http.ResponseWriter, req *http.Request) {
 	duration := float64(time.Since(t)) / float64(time.Millisecond)
 	h.logger.WithFields(log.Fields{
 		"host":              req.RemoteAddr,
-		"vhost":             req.Host,
+		"vhost":             getHost(req),
 		"request_protocol":  req.Proto,
 		"runtime":           fmt.Sprintf("%0.3f", duration),
 		"method":            req.Method,
diff --git a/outpost/pkg/proxy/oauth.go b/outpost/pkg/proxy/oauth.go
index 9ee0bcadd..9d1d894fa 100644
--- a/outpost/pkg/proxy/oauth.go
+++ b/outpost/pkg/proxy/oauth.go
@@ -161,7 +161,7 @@ func (p *OAuthProxy) OAuthStart(rw http.ResponseWriter, req *http.Request) {
 		p.ErrorPage(rw, http.StatusInternalServerError, "Internal Server Error", err.Error())
 		return
 	}
-	redirectURI := p.GetRedirectURI(req.Host)
+	redirectURI := p.GetRedirectURI(getHost(req))
 	http.Redirect(rw, req, p.provider.GetLoginURL(redirectURI, fmt.Sprintf("%v:%v", nonce, redirect)), http.StatusFound)
 }
 
@@ -184,7 +184,7 @@ func (p *OAuthProxy) OAuthCallback(rw http.ResponseWriter, req *http.Request) {
 		return
 	}
 
-	session, err := p.redeemCode(req.Context(), req.Host, req.Form.Get("code"))
+	session, err := p.redeemCode(req.Context(), getHost(req), req.Form.Get("code"))
 	if err != nil {
 		p.logger.Errorf("Error redeeming code during OAuth2 callback: %v", err)
 		p.ErrorPage(rw, http.StatusInternalServerError, "Internal Server Error", "Internal Error")
diff --git a/outpost/pkg/proxy/server.go b/outpost/pkg/proxy/server.go
index e01dbee95..44a355b51 100644
--- a/outpost/pkg/proxy/server.go
+++ b/outpost/pkg/proxy/server.go
@@ -42,7 +42,8 @@ func (s *Server) handler(w http.ResponseWriter, r *http.Request) {
 		w.WriteHeader(204)
 		return
 	}
-	handler, ok := s.Handlers[r.Host]
+	host := getHost(r)
+	handler, ok := s.Handlers[host]
 	if !ok {
 		// If we only have one handler, host name switching doesn't matter
 		if len(s.Handlers) == 1 {
@@ -56,7 +57,7 @@ func (s *Server) handler(w http.ResponseWriter, r *http.Request) {
 		for k := range s.Handlers {
 			hostKeys = append(hostKeys, k)
 		}
-		s.logger.WithField("host", r.Host).WithField("known-hosts", strings.Join(hostKeys, ", ")).Debug("Host header does not match any we know of")
+		s.logger.WithField("host", host).WithField("known-hosts", strings.Join(hostKeys, ", ")).Debug("Host header does not match any we know of")
 		w.WriteHeader(404)
 		return
 	}
diff --git a/outpost/pkg/proxy/utils.go b/outpost/pkg/proxy/utils.go
new file mode 100644
index 000000000..d9e4602a9
--- /dev/null
+++ b/outpost/pkg/proxy/utils.go
@@ -0,0 +1,12 @@
+package proxy
+
+import "net/http"
+
+var xForwardedHost = http.CanonicalHeaderKey("X-Forwarded-Host")
+
+func getHost(req *http.Request) string {
+	if req.Header.Get(xForwardedHost) != "" {
+		return req.Header.Get(xForwardedHost)
+	}
+	return req.Host
+}