diff --git a/go.mod b/go.mod
index 128904a9b..4ee2e3332 100644
--- a/go.mod
+++ b/go.mod
@@ -26,6 +26,7 @@ require (
 	github.com/sirupsen/logrus v1.9.0
 	github.com/stretchr/testify v1.8.1
 	goauthentik.io/api/v3 v3.2023012.5
+	golang.org/x/exp v0.0.0-20230210204819-062eb4c674ab
 	golang.org/x/oauth2 v0.0.0-20220223155221-ee480838109b
 	golang.org/x/sync v0.0.0-20220601150217-0de741cfad7f
 	gopkg.in/boj/redistore.v1 v1.0.0-20160128113310-fc113767cd6b
@@ -71,7 +72,7 @@ require (
 	go.opentelemetry.io/otel/trace v1.11.1 // indirect
 	golang.org/x/crypto v0.0.0-20220926161630-eccd6366d1be // indirect
 	golang.org/x/net v0.0.0-20221002022538-bcab6841153b // indirect
-	golang.org/x/sys v0.0.0-20220928140112-f11e5e49a4ec // indirect
+	golang.org/x/sys v0.1.0 // indirect
 	golang.org/x/text v0.3.7 // indirect
 	google.golang.org/appengine v1.6.7 // indirect
 	google.golang.org/protobuf v1.28.1 // indirect
diff --git a/go.sum b/go.sum
index 8f49100d5..5cceb0664 100644
--- a/go.sum
+++ b/go.sum
@@ -405,6 +405,8 @@ golang.org/x/exp v0.0.0-20191227195350-da58074b4299/go.mod h1:2RIsYlXP63K8oxa1u0
 golang.org/x/exp v0.0.0-20200119233911-0405dc783f0a/go.mod h1:2RIsYlXP63K8oxa1u096TMicItID8zy7Y6sNkU49FU4=
 golang.org/x/exp v0.0.0-20200207192155-f17229e696bd/go.mod h1:J/WKrq2StrnmMY6+EHIKF9dgMWnmCNThgcyBT1FY9mM=
 golang.org/x/exp v0.0.0-20200224162631-6cc2880d07d6/go.mod h1:3jZMyOhIsHpP37uCMkUooju7aAi5cS1Q23tOzKc+0MU=
+golang.org/x/exp v0.0.0-20230210204819-062eb4c674ab h1:628ME69lBm9C6JY2wXhAph/yjN3jezx1z7BIDLUwxjo=
+golang.org/x/exp v0.0.0-20230210204819-062eb4c674ab/go.mod h1:CxIveKay+FTh1D0yPZemJVgC/95VzuuOLq5Qi4xnoYc=
 golang.org/x/image v0.0.0-20190227222117-0694c2d4d067/go.mod h1:kZ7UVZpmo3dzQBMxlp+ypCbDeSB+sBbTgSJuh5dn5js=
 golang.org/x/image v0.0.0-20190802002840-cff245a6509b/go.mod h1:FeLwcggjj3mMvU+oOTbSwawSJRM1uh48EjtB4UJZlP0=
 golang.org/x/lint v0.0.0-20181026193005-c67002cb31c3/go.mod h1:UVdnD1Gm6xHRNCYTkRU2/jEulfH38KcIWyp/GAMgvoE=
@@ -528,6 +530,8 @@ golang.org/x/sys v0.0.0-20220114195835-da31bd327af9/go.mod h1:oPkhp1MJrh7nUepCBc
 golang.org/x/sys v0.0.0-20220715151400-c0bba94af5f8/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.0.0-20220928140112-f11e5e49a4ec h1:BkDtF2Ih9xZ7le9ndzTA7KJow28VbQW3odyk/8drmuI=
 golang.org/x/sys v0.0.0-20220928140112-f11e5e49a4ec/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
+golang.org/x/sys v0.1.0 h1:kunALQeHf1/185U1i0GOB/fy1IPRDDpuoOOqRReG57U=
+golang.org/x/sys v0.1.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/term v0.0.0-20201126162022-7de9c90e9dd1/go.mod h1:bj7SfCRtBDWHUb9snDiAeCFNEtKQo2Wmx5Cou7ajbmo=
 golang.org/x/term v0.0.0-20210927222741-03fcf44c2211/go.mod h1:jbD1KX2456YbFQfuXm/mYQcufACuNUgVhRMnK/tPxf8=
 golang.org/x/text v0.0.0-20170915032832-14c0d48ead0c/go.mod h1:NqM8EUOU14njkJ3fqMW+pc6Ldnwhi/IjpwHt7yyuwOQ=
@@ -587,6 +591,7 @@ golang.org/x/tools v0.0.0-20200729194436-6467de6f59a7/go.mod h1:njjCfa9FT2d7l9Bc
 golang.org/x/tools v0.0.0-20200804011535-6c149bb5ef0d/go.mod h1:njjCfa9FT2d7l9Bc6FUM5FLjQPp3cFF28FI3qnDFljA=
 golang.org/x/tools v0.0.0-20200825202427-b303f430e36d/go.mod h1:njjCfa9FT2d7l9Bc6FUM5FLjQPp3cFF28FI3qnDFljA=
 golang.org/x/tools v0.0.0-20210112230658-8b4aab62c064 h1:BmCFkEH4nJrYcAc2L08yX5RhYGD4j58PTMkEUDkpz2I=
+golang.org/x/tools v0.2.0 h1:G6AHpWxTMGY1KyEYoAQ5WTtIekUUvDNjan3ugu60JvE=
 golang.org/x/xerrors v0.0.0-20190717185122-a985d3407aa7/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 golang.org/x/xerrors v0.0.0-20191011141410-1b5146add898/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 golang.org/x/xerrors v0.0.0-20191204190536-9bdfabe68543/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
diff --git a/internal/outpost/proxyv2/application/application.go b/internal/outpost/proxyv2/application/application.go
index 47ac2a5e3..f00720631 100644
--- a/internal/outpost/proxyv2/application/application.go
+++ b/internal/outpost/proxyv2/application/application.go
@@ -2,6 +2,7 @@ package application
 
 import (
 	"context"
+	"crypto/sha256"
 	"crypto/tls"
 	"encoding/gob"
 	"fmt"
@@ -40,6 +41,7 @@ type Application struct {
 	oauthConfig   oauth2.Config
 	tokenVerifier *oidc.IDTokenVerifier
 	outpostName   string
+	sessionName   string
 
 	sessions    sessions.Store
 	proxyConfig api.ProxyOutpostConfig
@@ -48,12 +50,19 @@ type Application struct {
 	log *log.Entry
 	mux *mux.Router
 	ak  *ak.APIController
+	srv Server
 
 	errorTemplates  *template.Template
 	authHeaderCache *ttlcache.Cache[string, Claims]
 }
 
-func NewApplication(p api.ProxyOutpostConfig, c *http.Client, cs *ak.CryptoStore, ak *ak.APIController) (*Application, error) {
+type Server interface {
+	API() *ak.APIController
+	Apps() []*Application
+	CryptoStore() *ak.CryptoStore
+}
+
+func NewApplication(p api.ProxyOutpostConfig, c *http.Client, server Server) (*Application, error) {
 	gob.Register(Claims{})
 	muxLogger := log.WithField("logger", "authentik.outpost.proxyv2.application").WithField("name", p.Name)
 
@@ -77,13 +86,13 @@ func NewApplication(p api.ProxyOutpostConfig, c *http.Client, cs *ak.CryptoStore
 	}.Encode()
 
 	managed := false
-	if m := ak.Outpost.Managed.Get(); m != nil {
+	if m := server.API().Outpost.Managed.Get(); m != nil {
 		managed = *m == "goauthentik.io/outposts/embedded"
 	}
 	// Configure an OpenID Connect aware OAuth2 client.
 	endpoint := GetOIDCEndpoint(
 		p,
-		ak.Outpost.Config["authentik_host"].(string),
+		server.API().Outpost.Config["authentik_host"].(string),
 		managed,
 	)
 
@@ -100,10 +109,16 @@ func NewApplication(p api.ProxyOutpostConfig, c *http.Client, cs *ak.CryptoStore
 		Scopes:       p.ScopesToRequest,
 	}
 	mux := mux.NewRouter()
+
+	h := sha256.New()
+	bs := string(h.Sum([]byte(*p.ClientId)))
+	sessionName := fmt.Sprintf("authentik_proxy_%s", bs[:8])
+
 	a := &Application{
 		Host:            externalHost.Host,
 		log:             muxLogger,
-		outpostName:     ak.Outpost.Name,
+		outpostName:     server.API().Outpost.Name,
+		sessionName:     sessionName,
 		endpoint:        endpoint,
 		oauthConfig:     oauth2Config,
 		tokenVerifier:   verifier,
@@ -111,8 +126,9 @@ func NewApplication(p api.ProxyOutpostConfig, c *http.Client, cs *ak.CryptoStore
 		httpClient:      c,
 		mux:             mux,
 		errorTemplates:  templates.GetTemplates(),
-		ak:              ak,
+		ak:              server.API(),
 		authHeaderCache: ttlcache.New(ttlcache.WithDisableTouchOnHit[string, Claims]()),
+		srv:             server,
 	}
 	go a.authHeaderCache.Start()
 	a.sessions = a.getStore(p, externalHost)
@@ -153,7 +169,9 @@ func NewApplication(p api.ProxyOutpostConfig, c *http.Client, cs *ak.CryptoStore
 			}).Observe(float64(after))
 		})
 	})
-	mux.Use(sentryhttp.New(sentryhttp.Options{}).Handle)
+	if server.API().GlobalConfig.ErrorReporting.Enabled {
+		mux.Use(sentryhttp.New(sentryhttp.Options{}).Handle)
+	}
 	mux.Use(func(inner http.Handler) http.Handler {
 		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 			if strings.EqualFold(r.URL.Query().Get(CallbackSignature), "true") {
@@ -184,11 +202,11 @@ func NewApplication(p api.ProxyOutpostConfig, c *http.Client, cs *ak.CryptoStore
 	}
 
 	if kp := p.Certificate.Get(); kp != nil {
-		err := cs.AddKeypair(*kp)
+		err := server.CryptoStore().AddKeypair(*kp)
 		if err != nil {
 			return nil, fmt.Errorf("failed to initially fetch certificate: %w", err)
 		}
-		a.Cert = cs.Get(*kp)
+		a.Cert = server.CryptoStore().Get(*kp)
 	}
 
 	if *p.SkipPathRegex != "" {
@@ -235,7 +253,7 @@ func (a *Application) Stop() {
 
 func (a *Application) handleSignOut(rw http.ResponseWriter, r *http.Request) {
 	redirect := a.endpoint.EndSessionEndpoint
-	s, err := a.sessions.Get(r, constants.SessionName)
+	s, err := a.sessions.Get(r, a.SessionName())
 	if err != nil {
 		a.redirectToStart(rw, r)
 		return
diff --git a/internal/outpost/proxyv2/application/auth.go b/internal/outpost/proxyv2/application/auth.go
index a6ab22c75..a17ee4536 100644
--- a/internal/outpost/proxyv2/application/auth.go
+++ b/internal/outpost/proxyv2/application/auth.go
@@ -49,7 +49,7 @@ func (a *Application) checkAuth(rw http.ResponseWriter, r *http.Request) (*Claim
 }
 
 func (a *Application) getClaimsFromSession(r *http.Request) *Claims {
-	s, err := a.sessions.Get(r, constants.SessionName)
+	s, err := a.sessions.Get(r, a.SessionName())
 	if err != nil {
 		// err == user has no session/session is not valid, reject
 		return nil
@@ -77,7 +77,7 @@ func (a *Application) getClaimsFromCache(r *http.Request) *Claims {
 }
 
 func (a *Application) saveAndCacheClaims(rw http.ResponseWriter, r *http.Request, claims Claims) (*Claims, error) {
-	s, _ := a.sessions.Get(r, constants.SessionName)
+	s, _ := a.sessions.Get(r, a.SessionName())
 
 	s.Values[constants.SessionClaims] = claims
 	err := s.Save(r, rw)
diff --git a/internal/outpost/proxyv2/application/error.go b/internal/outpost/proxyv2/application/error.go
index 327e24a4f..8db0b48c3 100644
--- a/internal/outpost/proxyv2/application/error.go
+++ b/internal/outpost/proxyv2/application/error.go
@@ -20,7 +20,7 @@ func (a *Application) ErrorPage(rw http.ResponseWriter, r *http.Request, err str
 		Message:     "Error proxying to upstream server",
 		ProxyPrefix: "/outpost.goauthentik.io",
 	}
-	if claims != nil && claims.Proxy.IsSuperuser {
+	if claims != nil && claims.Proxy != nil && claims.Proxy.IsSuperuser {
 		data.Message = err
 	} else {
 		data.Message = "Failed to connect to backend."
diff --git a/internal/outpost/proxyv2/application/mode_forward.go b/internal/outpost/proxyv2/application/mode_forward.go
index 757d7fbe6..47b5dd47b 100644
--- a/internal/outpost/proxyv2/application/mode_forward.go
+++ b/internal/outpost/proxyv2/application/mode_forward.go
@@ -64,7 +64,7 @@ func (a *Application) forwardHandleTraefik(rw http.ResponseWriter, r *http.Reque
 	// to a (possibly) different domain, but we want to be redirected back
 	// to the application
 	// X-Forwarded-Uri is only the path, so we need to build the entire URL
-	s, _ := a.sessions.Get(r, constants.SessionName)
+	s, _ := a.sessions.Get(r, a.SessionName())
 	if _, redirectSet := s.Values[constants.SessionRedirect]; !redirectSet {
 		s.Values[constants.SessionRedirect] = fwd.String()
 		err = s.Save(r, rw)
@@ -115,7 +115,7 @@ func (a *Application) forwardHandleCaddy(rw http.ResponseWriter, r *http.Request
 	// to a (possibly) different domain, but we want to be redirected back
 	// to the application
 	// X-Forwarded-Uri is only the path, so we need to build the entire URL
-	s, _ := a.sessions.Get(r, constants.SessionName)
+	s, _ := a.sessions.Get(r, a.SessionName())
 	if _, redirectSet := s.Values[constants.SessionRedirect]; !redirectSet {
 		s.Values[constants.SessionRedirect] = fwd.String()
 		err = s.Save(r, rw)
@@ -151,7 +151,7 @@ func (a *Application) forwardHandleNginx(rw http.ResponseWriter, r *http.Request
 		return
 	}
 
-	s, _ := a.sessions.Get(r, constants.SessionName)
+	s, _ := a.sessions.Get(r, a.SessionName())
 	if _, redirectSet := s.Values[constants.SessionRedirect]; !redirectSet {
 		s.Values[constants.SessionRedirect] = fwd.String()
 		err = s.Save(r, rw)
@@ -190,7 +190,7 @@ func (a *Application) forwardHandleEnvoy(rw http.ResponseWriter, r *http.Request
 	// to a (possibly) different domain, but we want to be redirected back
 	// to the application
 	// X-Forwarded-Uri is only the path, so we need to build the entire URL
-	s, _ := a.sessions.Get(r, constants.SessionName)
+	s, _ := a.sessions.Get(r, a.SessionName())
 	if _, redirectSet := s.Values[constants.SessionRedirect]; !redirectSet {
 		s.Values[constants.SessionRedirect] = fwd.String()
 		err = s.Save(r, rw)
diff --git a/internal/outpost/proxyv2/application/mode_forward_caddy_test.go b/internal/outpost/proxyv2/application/mode_forward_caddy_test.go
index 099018c8d..b762ce8e7 100644
--- a/internal/outpost/proxyv2/application/mode_forward_caddy_test.go
+++ b/internal/outpost/proxyv2/application/mode_forward_caddy_test.go
@@ -48,7 +48,7 @@ func TestForwardHandleCaddy_Single_Headers(t *testing.T) {
 
 	assert.Equal(t, http.StatusFound, rr.Code)
 	loc, _ := rr.Result().Location()
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	shouldUrl := url.Values{
 		"client_id":     []string{*a.proxyConfig.ClientId},
 		"redirect_uri":  []string{"https://ext.t.goauthentik.io/outpost.goauthentik.io/callback?X-authentik-auth-callback=true"},
@@ -69,7 +69,7 @@ func TestForwardHandleCaddy_Single_Claims(t *testing.T) {
 	rr := httptest.NewRecorder()
 	a.forwardHandleCaddy(rr, req)
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	s.ID = uuid.New().String()
 	s.Options.MaxAge = 86400
 	s.Values[constants.SessionClaims] = Claims{
@@ -135,7 +135,7 @@ func TestForwardHandleCaddy_Domain_Header(t *testing.T) {
 
 	assert.Equal(t, http.StatusFound, rr.Code)
 	loc, _ := rr.Result().Location()
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	shouldUrl := url.Values{
 		"client_id":     []string{*a.proxyConfig.ClientId},
 		"redirect_uri":  []string{"https://ext.t.goauthentik.io/outpost.goauthentik.io/callback?X-authentik-auth-callback=true"},
diff --git a/internal/outpost/proxyv2/application/mode_forward_envoy_test.go b/internal/outpost/proxyv2/application/mode_forward_envoy_test.go
index cfca8a991..a55314247 100644
--- a/internal/outpost/proxyv2/application/mode_forward_envoy_test.go
+++ b/internal/outpost/proxyv2/application/mode_forward_envoy_test.go
@@ -33,7 +33,7 @@ func TestForwardHandleEnvoy_Single_Headers(t *testing.T) {
 
 	assert.Equal(t, http.StatusFound, rr.Code)
 	loc, _ := rr.Result().Location()
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	shouldUrl := url.Values{
 		"client_id":     []string{*a.proxyConfig.ClientId},
 		"redirect_uri":  []string{"https://ext.t.goauthentik.io/outpost.goauthentik.io/callback?X-authentik-auth-callback=true"},
@@ -51,7 +51,7 @@ func TestForwardHandleEnvoy_Single_Claims(t *testing.T) {
 	rr := httptest.NewRecorder()
 	a.forwardHandleEnvoy(rr, req)
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	s.ID = uuid.New().String()
 	s.Options.MaxAge = 86400
 	s.Values[constants.SessionClaims] = Claims{
@@ -103,7 +103,7 @@ func TestForwardHandleEnvoy_Domain_Header(t *testing.T) {
 
 	assert.Equal(t, http.StatusFound, rr.Code)
 	loc, _ := rr.Result().Location()
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 
 	shouldUrl := url.Values{
 		"client_id":     []string{*a.proxyConfig.ClientId},
diff --git a/internal/outpost/proxyv2/application/mode_forward_nginx_test.go b/internal/outpost/proxyv2/application/mode_forward_nginx_test.go
index 74c9f58b3..13eaa6231 100644
--- a/internal/outpost/proxyv2/application/mode_forward_nginx_test.go
+++ b/internal/outpost/proxyv2/application/mode_forward_nginx_test.go
@@ -42,7 +42,7 @@ func TestForwardHandleNginx_Single_Headers(t *testing.T) {
 
 	assert.Equal(t, http.StatusUnauthorized, rr.Code)
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	assert.Equal(t, "http://test.goauthentik.io/app", s.Values[constants.SessionRedirect])
 }
 
@@ -56,7 +56,7 @@ func TestForwardHandleNginx_Single_URI(t *testing.T) {
 
 	assert.Equal(t, http.StatusUnauthorized, rr.Code)
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	assert.Equal(t, "/app", s.Values[constants.SessionRedirect])
 }
 
@@ -68,7 +68,7 @@ func TestForwardHandleNginx_Single_Claims(t *testing.T) {
 	rr := httptest.NewRecorder()
 	a.forwardHandleNginx(rr, req)
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	s.ID = uuid.New().String()
 	s.Options.MaxAge = 86400
 	s.Values[constants.SessionClaims] = Claims{
@@ -132,6 +132,6 @@ func TestForwardHandleNginx_Domain_Header(t *testing.T) {
 
 	assert.Equal(t, http.StatusUnauthorized, rr.Code)
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	assert.Equal(t, "http://test.goauthentik.io/app", s.Values[constants.SessionRedirect])
 }
diff --git a/internal/outpost/proxyv2/application/mode_forward_traefik_test.go b/internal/outpost/proxyv2/application/mode_forward_traefik_test.go
index 3820114b7..6b3b20c82 100644
--- a/internal/outpost/proxyv2/application/mode_forward_traefik_test.go
+++ b/internal/outpost/proxyv2/application/mode_forward_traefik_test.go
@@ -48,7 +48,7 @@ func TestForwardHandleTraefik_Single_Headers(t *testing.T) {
 
 	assert.Equal(t, http.StatusFound, rr.Code)
 	loc, _ := rr.Result().Location()
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	shouldUrl := url.Values{
 		"client_id":     []string{*a.proxyConfig.ClientId},
 		"redirect_uri":  []string{"https://ext.t.goauthentik.io/outpost.goauthentik.io/callback?X-authentik-auth-callback=true"},
@@ -69,7 +69,7 @@ func TestForwardHandleTraefik_Single_Claims(t *testing.T) {
 	rr := httptest.NewRecorder()
 	a.forwardHandleTraefik(rr, req)
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	s.ID = uuid.New().String()
 	s.Options.MaxAge = 86400
 	s.Values[constants.SessionClaims] = Claims{
@@ -135,7 +135,7 @@ func TestForwardHandleTraefik_Domain_Header(t *testing.T) {
 
 	assert.Equal(t, http.StatusFound, rr.Code)
 	loc, _ := rr.Result().Location()
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	shouldUrl := url.Values{
 		"client_id":     []string{*a.proxyConfig.ClientId},
 		"redirect_uri":  []string{"https://ext.t.goauthentik.io/outpost.goauthentik.io/callback?X-authentik-auth-callback=true"},
diff --git a/internal/outpost/proxyv2/application/mode_proxy_test.go b/internal/outpost/proxyv2/application/mode_proxy_test.go
index 5f4d54427..a33f7cb96 100644
--- a/internal/outpost/proxyv2/application/mode_proxy_test.go
+++ b/internal/outpost/proxyv2/application/mode_proxy_test.go
@@ -70,7 +70,7 @@ func TestProxy_ModifyRequest_Claims(t *testing.T) {
 	}
 	rr := httptest.NewRecorder()
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	s.ID = uuid.New().String()
 	s.Options.MaxAge = 86400
 	s.Values[constants.SessionClaims] = Claims{
@@ -100,7 +100,7 @@ func TestProxy_ModifyRequest_Claims_Invalid(t *testing.T) {
 	}
 	rr := httptest.NewRecorder()
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	s.ID = uuid.New().String()
 	s.Options.MaxAge = 86400
 	s.Values[constants.SessionClaims] = Claims{
diff --git a/internal/outpost/proxyv2/application/oauth.go b/internal/outpost/proxyv2/application/oauth.go
index 19ab591cc..41f3f311b 100644
--- a/internal/outpost/proxyv2/application/oauth.go
+++ b/internal/outpost/proxyv2/application/oauth.go
@@ -45,7 +45,7 @@ func (a *Application) checkRedirectParam(r *http.Request) (string, bool) {
 
 func (a *Application) handleAuthStart(rw http.ResponseWriter, r *http.Request) {
 	newState := base64.RawURLEncoding.EncodeToString(securecookie.GenerateRandomKey(32))
-	s, _ := a.sessions.Get(r, constants.SessionName)
+	s, _ := a.sessions.Get(r, a.SessionName())
 	// Check if we already have a state in the session,
 	// and if we do we don't do anything here
 	currentState, ok := s.Values[constants.SessionOAuthState].(string)
@@ -74,7 +74,7 @@ func (a *Application) handleAuthStart(rw http.ResponseWriter, r *http.Request) {
 }
 
 func (a *Application) handleAuthCallback(rw http.ResponseWriter, r *http.Request) {
-	s, err := a.sessions.Get(r, constants.SessionName)
+	s, err := a.sessions.Get(r, a.SessionName())
 	if err != nil {
 		a.log.WithError(err).Trace("failed to get session")
 	}
diff --git a/internal/outpost/proxyv2/application/session.go b/internal/outpost/proxyv2/application/session.go
index 8a3a7f944..5861df8cb 100644
--- a/internal/outpost/proxyv2/application/session.go
+++ b/internal/outpost/proxyv2/application/session.go
@@ -14,6 +14,7 @@ import (
 	"github.com/gorilla/sessions"
 	"goauthentik.io/api/v3"
 	"goauthentik.io/internal/config"
+	"goauthentik.io/internal/outpost/proxyv2/codecs"
 	"goauthentik.io/internal/outpost/proxyv2/constants"
 	"gopkg.in/boj/redistore.v1"
 )
@@ -21,50 +22,55 @@ import (
 const RedisKeyPrefix = "authentik_proxy_session_"
 
 func (a *Application) getStore(p api.ProxyOutpostConfig, externalHost *url.URL) sessions.Store {
-	var store sessions.Store
-	if config.Get().Redis.Host != "" {
-		rs, err := redistore.NewRediStoreWithDB(10, "tcp", fmt.Sprintf("%s:%d", config.Get().Redis.Host, config.Get().Redis.Port), config.Get().Redis.Password, strconv.Itoa(config.Get().Redis.DB), []byte(*p.CookieSecret))
+	maxAge := 0
+	if p.AccessTokenValidity.IsSet() {
+		t := p.AccessTokenValidity.Get()
+		// Add one to the validity to ensure we don't have a session with indefinite length
+		maxAge = int(*t) + 1
+	}
+	if config.Get().Redis.Host == "foo" {
+		rs, err := redistore.NewRediStoreWithDB(10, "tcp", fmt.Sprintf("%s:%d", config.Get().Redis.Host, config.Get().Redis.Port), config.Get().Redis.Password, strconv.Itoa(config.Get().Redis.DB))
 		if err != nil {
 			panic(err)
 		}
+		rs.Codecs = codecs.CodecsFromPairs(maxAge, []byte(*p.CookieSecret))
 		rs.SetMaxLength(math.MaxInt)
 		rs.SetKeyPrefix(RedisKeyPrefix)
-		if p.AccessTokenValidity.IsSet() {
-			t := p.AccessTokenValidity.Get()
-			// Add one to the validity to ensure we don't have a session with indefinite length
-			rs.SetMaxAge(int(*t) + 1)
-		} else {
-			rs.SetMaxAge(0)
-		}
+
 		rs.Options.Domain = *p.CookieDomain
 		a.log.Trace("using redis session backend")
-		store = rs
-	} else {
-		dir := os.TempDir()
-		cs := sessions.NewFilesystemStore(dir, []byte(*p.CookieSecret))
-		// https://github.com/markbates/goth/commit/7276be0fdf719ddff753f3574ef0f967e4a5a5f7
-		// set the maxLength of the cookies stored on the disk to a larger number to prevent issues with:
-		// securecookie: the value is too long
-		// when using OpenID Connect , since this can contain a large amount of extra information in the id_token
-
-		// Note, when using the FilesystemStore only the session.ID is written to a browser cookie, so this is explicit for the storage on disk
-		cs.MaxLength(math.MaxInt)
-		if p.AccessTokenValidity.IsSet() {
-			t := p.AccessTokenValidity.Get()
-			// Add one to the validity to ensure we don't have a session with indefinite length
-			cs.MaxAge(int(*t) + 1)
-		} else {
-			cs.MaxAge(0)
-		}
-		cs.Options.Domain = *p.CookieDomain
-		a.log.WithField("dir", dir).Trace("using filesystem session backend")
-		store = cs
+		return rs
 	}
-	return store
+	dir := os.TempDir()
+	cs := sessions.NewFilesystemStore(dir)
+	cs.Codecs = codecs.CodecsFromPairs(maxAge, []byte(*p.CookieSecret))
+	// https://github.com/markbates/goth/commit/7276be0fdf719ddff753f3574ef0f967e4a5a5f7
+	// set the maxLength of the cookies stored on the disk to a larger number to prevent issues with:
+	// securecookie: the value is too long
+	// when using OpenID Connect , since this can contain a large amount of extra information in the id_token
+
+	// Note, when using the FilesystemStore only the session.ID is written to a browser cookie, so this is explicit for the storage on disk
+	cs.MaxLength(math.MaxInt)
+	cs.Options.Domain = *p.CookieDomain
+	a.log.WithField("dir", dir).Trace("using filesystem session backend")
+	return cs
+}
+
+func (a *Application) SessionName() string {
+	return a.sessionName
+}
+
+func (a *Application) getAllCodecs() []securecookie.Codec {
+	apps := a.srv.Apps()
+	cs := []securecookie.Codec{}
+	for _, app := range apps {
+		cs = append(cs, codecs.CodecsFromPairs(0, []byte(*app.proxyConfig.CookieSecret))...)
+	}
+	return cs
 }
 
 func (a *Application) Logout(sub string) error {
-	if fs, ok := a.sessions.(*sessions.FilesystemStore); ok {
+	if _, ok := a.sessions.(*sessions.FilesystemStore); ok {
 		files, err := os.ReadDir(os.TempDir())
 		if err != nil {
 			return err
@@ -81,8 +87,8 @@ func (a *Application) Logout(sub string) error {
 				continue
 			}
 			err = securecookie.DecodeMulti(
-				constants.SessionName, string(data),
-				&s.Values, fs.Codecs...,
+				a.SessionName(), string(data),
+				&s.Values, a.getAllCodecs()...,
 			)
 			if err != nil {
 				a.log.WithError(err).Trace("failed to decode session")
diff --git a/internal/outpost/proxyv2/application/session_test.go b/internal/outpost/proxyv2/application/session_test.go
index 5180e89a8..66ea11dd4 100644
--- a/internal/outpost/proxyv2/application/session_test.go
+++ b/internal/outpost/proxyv2/application/session_test.go
@@ -20,7 +20,7 @@ func TestLogout(t *testing.T) {
 	rr := httptest.NewRecorder()
 
 	// Login once
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	s.ID = uuid.New().String()
 	s.Options.MaxAge = 86400
 	s.Values[constants.SessionClaims] = Claims{
@@ -36,7 +36,7 @@ func TestLogout(t *testing.T) {
 	assert.Equal(t, http.StatusBadGateway, rr.Code)
 
 	// Login twice
-	s2, _ := a.sessions.Get(req, constants.SessionName)
+	s2, _ := a.sessions.Get(req, a.SessionName())
 	s2.ID = uuid.New().String()
 	s2.Options.MaxAge = 86400
 	s2.Values[constants.SessionClaims] = Claims{
@@ -53,7 +53,7 @@ func TestLogout(t *testing.T) {
 
 	// Logout
 	req, _ = http.NewRequest("GET", "https://ext.t.goauthentik.io/outpost.goauthentik.io/sign_out", nil)
-	s3, _ := a.sessions.Get(req, constants.SessionName)
+	s3, _ := a.sessions.Get(req, a.SessionName())
 	s3.ID = uuid.New().String()
 	s3.Options.MaxAge = 86400
 	s3.Values[constants.SessionClaims] = Claims{
diff --git a/internal/outpost/proxyv2/application/test.go b/internal/outpost/proxyv2/application/test.go
index 300715e23..b2d693ac0 100644
--- a/internal/outpost/proxyv2/application/test.go
+++ b/internal/outpost/proxyv2/application/test.go
@@ -7,7 +7,39 @@ import (
 	"goauthentik.io/internal/outpost/ak"
 )
 
+type testServer struct {
+	api  *ak.APIController
+	apps []*Application
+}
+
+func newTestServer() *testServer {
+	return &testServer{
+		api: ak.MockAK(
+			api.Outpost{
+				Config: map[string]interface{}{
+					"authentik_host": ak.TestSecret(),
+				},
+			},
+			ak.MockConfig(),
+		),
+		apps: make([]*Application, 0),
+	}
+}
+
+func (ts *testServer) API() *ak.APIController {
+	return ts.api
+}
+
+func (ts *testServer) CryptoStore() *ak.CryptoStore {
+	return nil
+}
+
+func (ts *testServer) Apps() []*Application {
+	return ts.apps
+}
+
 func newTestApplication() *Application {
+	ts := newTestServer()
 	a, _ := NewApplication(
 		api.ProxyOutpostConfig{
 			Name:                       ak.TestSecret(),
@@ -30,15 +62,8 @@ func newTestApplication() *Application {
 			},
 		},
 		http.DefaultClient,
-		nil,
-		ak.MockAK(
-			api.Outpost{
-				Config: map[string]interface{}{
-					"authentik_host": ak.TestSecret(),
-				},
-			},
-			ak.MockConfig(),
-		),
+		ts,
 	)
+	ts.apps = append(ts.apps, a)
 	return a
 }
diff --git a/internal/outpost/proxyv2/application/utils.go b/internal/outpost/proxyv2/application/utils.go
index 41e35b831..d895fa0be 100644
--- a/internal/outpost/proxyv2/application/utils.go
+++ b/internal/outpost/proxyv2/application/utils.go
@@ -30,7 +30,7 @@ func urlJoin(originalUrl string, newPath string) string {
 }
 
 func (a *Application) redirectToStart(rw http.ResponseWriter, r *http.Request) {
-	s, err := a.sessions.Get(r, constants.SessionName)
+	s, err := a.sessions.Get(r, a.SessionName())
 	if err != nil {
 		a.log.WithError(err).Warning("failed to decode session")
 	}
@@ -74,7 +74,7 @@ func (a *Application) redirectToStart(rw http.ResponseWriter, r *http.Request) {
 
 func (a *Application) redirect(rw http.ResponseWriter, r *http.Request) {
 	redirect := a.proxyConfig.ExternalHost
-	s, _ := a.sessions.Get(r, constants.SessionName)
+	s, _ := a.sessions.Get(r, a.SessionName())
 	redirectR, ok := s.Values[constants.SessionRedirect]
 	if ok {
 		redirect = redirectR.(string)
diff --git a/internal/outpost/proxyv2/application/utils_test.go b/internal/outpost/proxyv2/application/utils_test.go
index 252d9af51..7fa5518c4 100644
--- a/internal/outpost/proxyv2/application/utils_test.go
+++ b/internal/outpost/proxyv2/application/utils_test.go
@@ -23,7 +23,7 @@ func TestRedirectToStart_Proxy(t *testing.T) {
 	loc, _ := rr.Result().Location()
 	assert.Equal(t, "https://test.goauthentik.io/outpost.goauthentik.io/start?rd=https%3A%2F%2Ftest.goauthentik.io%2Ffoo%2Fbar%2Fbaz", loc.String())
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	assert.Equal(t, "https://test.goauthentik.io/foo/bar/baz", s.Values[constants.SessionRedirect])
 }
 
@@ -40,7 +40,7 @@ func TestRedirectToStart_Forward(t *testing.T) {
 	loc, _ := rr.Result().Location()
 	assert.Equal(t, "https://test.goauthentik.io/outpost.goauthentik.io/start?rd=https%3A%2F%2Ftest.goauthentik.io%2Ffoo%2Fbar%2Fbaz", loc.String())
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	assert.Equal(t, "https://test.goauthentik.io/foo/bar/baz", s.Values[constants.SessionRedirect])
 }
 
@@ -58,7 +58,7 @@ func TestRedirectToStart_Forward_Domain_Invalid(t *testing.T) {
 	loc, _ := rr.Result().Location()
 	assert.Equal(t, "https://test.goauthentik.io/outpost.goauthentik.io/start?rd=https%3A%2F%2Ftest.goauthentik.io", loc.String())
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	assert.Equal(t, "https://test.goauthentik.io", s.Values[constants.SessionRedirect])
 }
 
@@ -76,6 +76,6 @@ func TestRedirectToStart_Forward_Domain(t *testing.T) {
 	loc, _ := rr.Result().Location()
 	assert.Equal(t, "https://test.goauthentik.io/outpost.goauthentik.io/start?rd=https%3A%2F%2Ftest.goauthentik.io", loc.String())
 
-	s, _ := a.sessions.Get(req, constants.SessionName)
+	s, _ := a.sessions.Get(req, a.SessionName())
 	assert.Equal(t, "https://test.goauthentik.io", s.Values[constants.SessionRedirect])
 }
diff --git a/internal/outpost/proxyv2/codecs/codec.go b/internal/outpost/proxyv2/codecs/codec.go
new file mode 100644
index 000000000..472a25ed0
--- /dev/null
+++ b/internal/outpost/proxyv2/codecs/codec.go
@@ -0,0 +1,40 @@
+package codecs
+
+import (
+	"github.com/gorilla/securecookie"
+	log "github.com/sirupsen/logrus"
+)
+
+type Codec struct {
+	*securecookie.SecureCookie
+}
+
+func New(maxAge int, hashKey, blockKey []byte) *Codec {
+	cookie := securecookie.New(hashKey, blockKey)
+	cookie.MaxAge(maxAge)
+	return &Codec{
+		SecureCookie: cookie,
+	}
+}
+
+func CodecsFromPairs(maxAge int, keyPairs ...[]byte) []securecookie.Codec {
+	codecs := make([]securecookie.Codec, len(keyPairs)/2+len(keyPairs)%2)
+	for i := 0; i < len(keyPairs); i += 2 {
+		var blockKey []byte
+		if i+1 < len(keyPairs) {
+			blockKey = keyPairs[i+1]
+		}
+		codecs[i/2] = New(maxAge, keyPairs[i], blockKey)
+	}
+	return codecs
+}
+
+func (s *Codec) Encode(name string, value interface{}) (string, error) {
+	log.Trace("cookie encode")
+	return s.SecureCookie.Encode("authentik_proxy", value)
+}
+
+func (s *Codec) Decode(name string, value string, dst interface{}) error {
+	log.Trace("cookie decode")
+	return s.SecureCookie.Decode("authentik_proxy", value, dst)
+}
diff --git a/internal/outpost/proxyv2/constants/constants.go b/internal/outpost/proxyv2/constants/constants.go
index 837a19602..cdb3fcffe 100644
--- a/internal/outpost/proxyv2/constants/constants.go
+++ b/internal/outpost/proxyv2/constants/constants.go
@@ -1,7 +1,5 @@
 package constants
 
-const SessionName = "authentik_proxy"
-
 const SessionOAuthState = "oauth_state"
 const SessionClaims = "claims"
 
diff --git a/internal/outpost/proxyv2/proxyv2.go b/internal/outpost/proxyv2/proxyv2.go
index 1271c39bf..11338fcc6 100644
--- a/internal/outpost/proxyv2/proxyv2.go
+++ b/internal/outpost/proxyv2/proxyv2.go
@@ -50,7 +50,9 @@ func NewProxyServer(ac *ak.APIController) *ProxyServer {
 
 	globalMux := rootMux.NewRoute().Subrouter()
 	globalMux.Use(web.NewLoggingHandler(l.WithField("logger", "authentik.outpost.proxyv2.http"), nil))
-	globalMux.Use(sentryhttp.New(sentryhttp.Options{}).Handle)
+	if ac.GlobalConfig.ErrorReporting.Enabled {
+		globalMux.Use(sentryhttp.New(sentryhttp.Options{}).Handle)
+	}
 	s := &ProxyServer{
 		cryptoStore: ak.NewCryptoStore(ac.Client.CryptoApi),
 		apps:        make(map[string]*application.Application),
diff --git a/internal/outpost/proxyv2/refresh.go b/internal/outpost/proxyv2/refresh.go
index 2db85e76e..357044c46 100644
--- a/internal/outpost/proxyv2/refresh.go
+++ b/internal/outpost/proxyv2/refresh.go
@@ -10,6 +10,7 @@ import (
 	"goauthentik.io/internal/outpost/ak"
 	"goauthentik.io/internal/outpost/proxyv2/application"
 	"goauthentik.io/internal/utils/web"
+	"golang.org/x/exp/maps"
 )
 
 func (ps *ProxyServer) Refresh() error {
@@ -33,7 +34,7 @@ func (ps *ProxyServer) Refresh() error {
 				),
 			),
 		}
-		a, err := application.NewApplication(provider, hc, ps.cryptoStore, ps.akAPI)
+		a, err := application.NewApplication(provider, hc, ps)
 		existing, ok := apps[a.Host]
 		if ok {
 			existing.Stop()
@@ -48,3 +49,15 @@ func (ps *ProxyServer) Refresh() error {
 	ps.log.Debug("Swapped maps")
 	return nil
 }
+
+func (ps *ProxyServer) API() *ak.APIController {
+	return ps.akAPI
+}
+
+func (ps *ProxyServer) CryptoStore() *ak.CryptoStore {
+	return ps.cryptoStore
+}
+
+func (ps *ProxyServer) Apps() []*application.Application {
+	return maps.Values(ps.apps)
+}