diff --git a/cmd/server/main.go b/cmd/server/main.go
index 090dfa8ee..ecb3b1d2f 100644
--- a/cmd/server/main.go
+++ b/cmd/server/main.go
@@ -73,17 +73,14 @@ func main() {
 		}
 	}
 	go web.RunMetricsServer()
-	for {
-		go attemptStartBackend(g)
-		ws.Start()
-
-		<-ex
-		running = false
-		l.Info("shutting down gunicorn")
-		go g.Kill()
-		l.Info("shutting down webserver")
-		go ws.Shutdown()
-	}
+	go attemptStartBackend(g)
+	ws.Start()
+	<-ex
+	running = false
+	l.Info("shutting down gunicorn")
+	go g.Kill()
+	l.Info("shutting down webserver")
+	go ws.Shutdown()
 }
 
 func attemptStartBackend(g *gounicorn.GoUnicorn) {
diff --git a/internal/outpost/proxyv2/proxyv2.go b/internal/outpost/proxyv2/proxyv2.go
index cb2006fe0..a91e464cc 100644
--- a/internal/outpost/proxyv2/proxyv2.go
+++ b/internal/outpost/proxyv2/proxyv2.go
@@ -134,7 +134,7 @@ func (ps *ProxyServer) ServeHTTPS() {
 
 	ln, err := net.Listen("tcp", listenAddress)
 	if err != nil {
-		ps.log.WithError(err).Warning("Failed to listen for HTTPS")
+		ps.log.WithError(err).Warning("Failed to listen (TLS)")
 	}
 	proxyListener := &proxyproto.Listener{Listener: web.TCPKeepAliveListener{TCPListener: ln.(*net.TCPListener)}}
 	defer proxyListener.Close()
diff --git a/internal/web/tls.go b/internal/web/tls.go
index 32f07a944..6a1eb3785 100644
--- a/internal/web/tls.go
+++ b/internal/web/tls.go
@@ -40,7 +40,7 @@ func (ws *WebServer) listenTLS() {
 
 	ln, err := net.Listen("tcp", config.G.Web.ListenTLS)
 	if err != nil {
-		ws.log.WithError(err).Fatalf("failed to listen")
+		ws.log.WithError(err).Fatalf("failed to listen (TLS)")
 		return
 	}
 	proxyListener := &proxyproto.Listener{Listener: web.TCPKeepAliveListener{TCPListener: ln.(*net.TCPListener)}}