diff --git a/websocket.go b/websocket.go
index 3396fc6..c791722 100644
--- a/websocket.go
+++ b/websocket.go
@@ -19,13 +19,14 @@ import (
 )
 
 const (
-	TokenExpiringEvent  = "token expiring"
-	TokenExpiredEvent   = "token expired"
-	AuthenticationEvent = "auth"
-	SetStateEvent       = "set state"
-	SendServerLogsEvent = "send logs"
-	SendCommandEvent    = "send command"
-	ErrorEvent          = "daemon error"
+	AuthenticationSuccessEvent = "auth success"
+	TokenExpiringEvent         = "token expiring"
+	TokenExpiredEvent          = "token expired"
+	AuthenticationEvent        = "auth"
+	SetStateEvent              = "set state"
+	SendServerLogsEvent        = "send logs"
+	SendCommandEvent           = "send command"
+	ErrorEvent                 = "daemon error"
 )
 
 type WebsocketMessage struct {
@@ -140,14 +141,11 @@ func (wsh *WebsocketHandler) TokenValid() error {
 // Handle a request for a specific server websocket. This will handle inbound requests as well
 // as ensure that any console output is also passed down the wire on the socket.
 func (rt *Router) routeWebsocket(w http.ResponseWriter, r *http.Request, ps httprouter.Params) {
-	token, err := ParseJWT([]byte(r.URL.Query().Get("token")))
-	if err != nil {
-		return
-	}
-
 	c, err := rt.upgrader.Upgrade(w, r, nil)
 	if err != nil {
-		zap.S().Error(err)
+		zap.S().Errorw("error upgrading websocket", zap.Error(errors.WithStack(err)))
+		http.Error(w, "failed to upgrade websocket", http.StatusInternalServerError)
+
 		return
 	}
 
@@ -169,7 +167,7 @@ func (rt *Router) routeWebsocket(w http.ResponseWriter, r *http.Request, ps http
 		Server:     s,
 		Mutex:      sync.Mutex{},
 		Connection: c,
-		JWT:        token,
+		JWT:        nil,
 	}
 
 	handleOutput := func(data string) {
@@ -202,8 +200,6 @@ func (rt *Router) routeWebsocket(w http.ResponseWriter, r *http.Request, ps http
 	s.AddListener(server.StatsEvent, &handleResourceUse)
 	defer s.RemoveListener(server.StatsEvent, &handleResourceUse)
 
-	s.Emit(server.StatusEvent, s.State)
-
 	// Sit here and check the time to expiration on the JWT every 30 seconds until
 	// the token has expired. If we are within 3 minutes of the token expiring, send
 	// a notice over the socket that it is expiring soon. If it has expired, send that
@@ -262,6 +258,19 @@ func (rt *Router) routeWebsocket(w http.ResponseWriter, r *http.Request, ps http
 // concurrent writes to the connection, which would cause a runtime panic and cause
 // the program to crash out.
 func (wsh *WebsocketHandler) SendJson(v interface{}) error {
+	// Do not send JSON down the line if the JWT on the connection is not
+	// valid!
+	if err := wsh.TokenValid(); err != nil {
+		return nil
+	}
+
+	return wsh.unsafeSendJson(v)
+}
+
+// Sends JSON over the websocket connection, ignoring the authentication state of the
+// socket user. Do not call this directly unless you are positive a response should be
+// sent back to the client!
+func (wsh *WebsocketHandler) unsafeSendJson(v interface{}) error {
 	wsh.Mutex.Lock()
 	defer wsh.Mutex.Unlock()
 
@@ -315,10 +324,17 @@ func (wsh *WebsocketHandler) HandleInbound(m WebsocketMessage) error {
 		return errors.New("cannot handle websocket message, not an inbound connection")
 	}
 
-	if err := wsh.TokenValid(); err != nil {
-		zap.S().Debugw("jwt token is no longer valid", zap.String("message", err.Error()))
+	if m.Event != AuthenticationEvent {
+		if err := wsh.TokenValid(); err != nil {
+			zap.S().Debugw("jwt token is no longer valid", zap.String("message", err.Error()))
 
-		return nil
+			wsh.unsafeSendJson(WebsocketMessage{
+				Event: ErrorEvent,
+				Args:  []string{"could not authenticate client: " + err.Error()},
+			})
+
+			return nil
+		}
 	}
 
 	switch m.Event {
@@ -326,13 +342,22 @@ func (wsh *WebsocketHandler) HandleInbound(m WebsocketMessage) error {
 		{
 			token, err := ParseJWT([]byte(strings.Join(m.Args, "")))
 			if err != nil {
-				return nil
+				return err
 			}
 
 			if token.HasPermission(PermissionConnect) {
 				wsh.JWT = token
 			}
 
+			// On every authentication event, send the current server status back
+			// to the client. :)
+			wsh.Server.Emit(server.StatusEvent, wsh.Server.State)
+
+			wsh.unsafeSendJson(WebsocketMessage{
+				Event: AuthenticationSuccessEvent,
+				Args:  []string{},
+			})
+
 			return nil
 		}
 	case SetStateEvent: