diff --git a/cmd/server/main.go b/cmd/server/main.go
index 54d83d111..97a74558f 100644
--- a/cmd/server/main.go
+++ b/cmd/server/main.go
@@ -21,18 +21,19 @@ var running = true
 func main() {
 	log.SetLevel(log.DebugLevel)
 	log.SetFormatter(&log.JSONFormatter{})
+	l := log.WithField("logger", "authentik.root")
 	config.DefaultConfig()
 	err := config.LoadConfig("./authentik/lib/default.yml")
 	if err != nil {
-		log.WithError(err).Warning("failed to load default config")
+		l.WithError(err).Warning("failed to load default config")
 	}
 	err = config.LoadConfig("./local.env.yml")
 	if err != nil {
-		log.WithError(err).Debug("no local config to load")
+		l.WithError(err).Debug("no local config to load")
 	}
 	err = config.FromEnv()
 	if err != nil {
-		log.WithError(err).Debug("failed to environment variables")
+		l.WithError(err).Debug("failed to environment variables")
 	}
 	config.ConfigureLogger()
 
@@ -45,7 +46,7 @@ func main() {
 			Environment:      config.G.ErrorReporting.Environment,
 		})
 		if err != nil {
-			log.WithError(err).Warning("failed to init sentry")
+			l.WithError(err).Warning("failed to init sentry")
 		}
 	}
 
@@ -61,8 +62,6 @@ func main() {
 			go attemptProxyStart(ws, u)
 		}
 	}
-	defer g.Kill()
-	defer ws.Shutdown()
 	go web.RunMetricsServer()
 	for {
 		go attemptStartBackend(g)
@@ -70,19 +69,19 @@ func main() {
 
 		<-ex
 		running = false
-		log.WithField("logger", "authentik").Info("shutting down webserver")
+		l.WithField("logger", "authentik").Info("shutting down gunicorn")
+		go g.Kill()
+		l.WithField("logger", "authentik").Info("shutting down webserver")
 		go ws.Shutdown()
-		log.WithField("logger", "authentik").Info("killing gunicorn")
-		g.Kill()
 	}
 }
 
 func attemptStartBackend(g *gounicorn.GoUnicorn) {
 	for {
-		err := g.Start()
 		if !running {
 			return
 		}
+		err := g.Start()
 		log.WithField("logger", "authentik.router").WithError(err).Warning("gunicorn process died, restarting")
 	}
 }
diff --git a/internal/gounicorn/gounicorn.go b/internal/gounicorn/gounicorn.go
index ebe3890ae..a5b37b311 100644
--- a/internal/gounicorn/gounicorn.go
+++ b/internal/gounicorn/gounicorn.go
@@ -4,6 +4,8 @@ import (
 	"net/http"
 	"os"
 	"os/exec"
+	"runtime"
+	"syscall"
 	"time"
 
 	log "github.com/sirupsen/logrus"
@@ -49,7 +51,7 @@ func (g *GoUnicorn) IsRunning() bool {
 
 func (g *GoUnicorn) Start() error {
 	if g.killed {
-		g.log.Debug("Not restarting gunicorn since we're killed")
+		g.log.Debug("Not restarting gunicorn since we're shutdown")
 		return nil
 	}
 	if g.started {
@@ -91,8 +93,15 @@ func (g *GoUnicorn) healthcheck() {
 
 func (g *GoUnicorn) Kill() {
 	g.killed = true
-	err := g.p.Process.Kill()
+	var err error
+	if runtime.GOOS == "darwin" {
+		g.log.WithField("method", "kill").Warning("stopping gunicorn")
+		err = g.p.Process.Kill()
+	} else {
+		g.log.WithField("method", "sigterm").Warning("stopping gunicorn")
+		err = syscall.Kill(g.p.Process.Pid, syscall.SIGTERM)
+	}
 	if err != nil {
-		g.log.WithError(err).Warning("failed to kill gunicorn")
+		g.log.WithError(err).Warning("failed to stop gunicorn")
 	}
 }
diff --git a/internal/web/ssl.go b/internal/web/ssl.go
index ff6d0b455..c847b5467 100644
--- a/internal/web/ssl.go
+++ b/internal/web/ssl.go
@@ -26,7 +26,7 @@ func (ws *WebServer) listenTLS() {
 		ws.log.WithError(err).Fatalf("failed to listen")
 		return
 	}
-	ws.log.WithField("addr", config.G.Web.ListenTLS).Info("Running")
+	ws.log.WithField("addr", config.G.Web.ListenTLS).Info("Listening (TLS)")
 
 	proxyListener := &proxyproto.Listener{Listener: tcpKeepAliveListener{ln.(*net.TCPListener)}}
 	defer proxyListener.Close()
diff --git a/internal/web/web.go b/internal/web/web.go
index f265a2b6a..7f6a2846b 100644
--- a/internal/web/web.go
+++ b/internal/web/web.go
@@ -74,14 +74,13 @@ func (ws *WebServer) listenPlain() {
 	if err != nil {
 		ws.log.WithError(err).Fatalf("failed to listen")
 	}
-	ws.log.WithField("addr", config.G.Web.Listen).Info("Running")
+	ws.log.WithField("addr", config.G.Web.Listen).Info("Listening")
 
 	proxyListener := &proxyproto.Listener{Listener: ln}
 	defer proxyListener.Close()
 
 	ws.serve(proxyListener)
 
-	ws.log.WithField("addr", config.G.Web.Listen).Info("Running")
 	err = http.ListenAndServe(config.G.Web.Listen, ws.m)
 	if err != nil && !errors.Is(err, http.ErrServerClosed) {
 		ws.log.Errorf("ERROR: http.Serve() - %s", err)