diff --git a/authentik/lib/default.yml b/authentik/lib/default.yml
index 0613f82c5..d1488b6aa 100644
--- a/authentik/lib/default.yml
+++ b/authentik/lib/default.yml
@@ -68,6 +68,7 @@ outposts:
 
 cookie_domain: null
 disable_update_check: false
+disable_startup_analytics: false
 avatars: env://AUTHENTIK_AUTHENTIK__AVATARS?gravatar
 geoip: "./GeoLite2-City.mmdb"
 
diff --git a/authentik/root/settings.py b/authentik/root/settings.py
index 2966136c1..2b07dee85 100644
--- a/authentik/root/settings.py
+++ b/authentik/root/settings.py
@@ -437,19 +437,20 @@ if _ERROR_REPORTING:
         "Error reporting is enabled",
         env=CONFIG.y("error_reporting.environment", "customer"),
     )
-get_http_session().post(
-    "https://goauthentik.io/api/event",
-    json={
-        "domain": "authentik",
-        "name": "pageview",
-        "url": f"http://localhost/{env}",
-        "referrer": f"{__version__} ({build_hash})",
-    },
-    headers={
-        "User-Agent": sha512(SECRET_KEY.encode("ascii")).hexdigest()[:16],
-        "Content-Type": "text/plain",
-    },
-)
+if not CONFIG.y_bool("disable_startup_analytics", False):
+    get_http_session().post(
+        "https://goauthentik.io/api/event",
+        json={
+            "domain": "authentik",
+            "name": "pageview",
+            "url": f"http://localhost/{env}",
+            "referrer": f"{__version__} ({build_hash})",
+        },
+        headers={
+            "User-Agent": sha512(SECRET_KEY.encode("ascii")).hexdigest()[:16],
+            "Content-Type": "text/plain",
+        },
+    )
 
 # Static files (CSS, JavaScript, Images)
 # https://docs.djangoproject.com/en/2.1/howto/static-files/
diff --git a/cmd/server/main.go b/cmd/server/main.go
index 1a83f391a..54d83d111 100644
--- a/cmd/server/main.go
+++ b/cmd/server/main.go
@@ -56,15 +56,17 @@ func main() {
 
 	g := gounicorn.NewGoUnicorn()
 	ws := web.NewWebServer(g)
+	g.HealthyCallback = func() {
+		if !config.G.Web.DisableEmbeddedOutpost {
+			go attemptProxyStart(ws, u)
+		}
+	}
 	defer g.Kill()
 	defer ws.Shutdown()
 	go web.RunMetricsServer()
 	for {
 		go attemptStartBackend(g)
 		ws.Start()
-		if !config.G.Web.DisableEmbeddedOutpost {
-			go attemptProxyStart(ws, u)
-		}
 
 		<-ex
 		running = false
@@ -88,8 +90,6 @@ func attemptStartBackend(g *gounicorn.GoUnicorn) {
 func attemptProxyStart(ws *web.WebServer, u *url.URL) {
 	maxTries := 100
 	attempt := 0
-	// Sleep to wait for the app server to start
-	time.Sleep(30 * time.Second)
 	for {
 		log.WithField("logger", "authentik").Debug("attempting to init outpost")
 		ac := ak.NewAPIController(*u, config.G.SecretKey)
diff --git a/internal/gounicorn/gounicorn.go b/internal/gounicorn/gounicorn.go
index 3485ead23..ebe3890ae 100644
--- a/internal/gounicorn/gounicorn.go
+++ b/internal/gounicorn/gounicorn.go
@@ -11,6 +11,8 @@ import (
 )
 
 type GoUnicorn struct {
+	HealthyCallback func()
+
 	log     *log.Entry
 	p       *exec.Cmd
 	started bool
@@ -21,10 +23,11 @@ type GoUnicorn struct {
 func NewGoUnicorn() *GoUnicorn {
 	logger := log.WithField("logger", "authentik.router.unicorn")
 	g := &GoUnicorn{
-		log:     logger,
-		started: false,
-		killed:  false,
-		alive:   false,
+		log:             logger,
+		started:         false,
+		killed:          false,
+		alive:           false,
+		HealthyCallback: func() {},
 	}
 	g.initCmd()
 	return g
@@ -76,6 +79,7 @@ func (g *GoUnicorn) healthcheck() {
 	for range time.Tick(time.Second) {
 		if check() {
 			g.log.Info("backend is alive, backing off with healthchecks")
+			g.HealthyCallback()
 			break
 		}
 		g.log.Debug("backend not alive yet")