diff --git a/router/router_server_ws.go b/router/router_server_ws.go
index 8ab1411..22cfca7 100644
--- a/router/router_server_ws.go
+++ b/router/router_server_ws.go
@@ -5,6 +5,7 @@ import (
 	"encoding/json"
 	"time"
 
+	"emperror.dev/errors"
 	"github.com/gin-gonic/gin"
 	ws "github.com/gorilla/websocket"
 
@@ -24,12 +25,6 @@ var expectedCloseCodes = []int{
 func getServerWebsocket(c *gin.Context) {
 	manager := middleware.ExtractManager(c)
 	s, _ := manager.Get(c.Param("server"))
-	handler, err := websocket.GetHandler(s, c.Writer, c.Request)
-	if err != nil {
-		NewServerError(err, s).Abort(c)
-		return
-	}
-	defer handler.Connection.Close()
 
 	// Create a context that can be canceled when the user disconnects from this
 	// socket that will also cancel listeners running in separate threads. If the
@@ -38,10 +33,22 @@ func getServerWebsocket(c *gin.Context) {
 	ctx, cancel := context.WithCancel(c.Request.Context())
 	defer cancel()
 
+	handler, err := websocket.GetHandler(s, c.Writer, c.Request)
+	if err != nil {
+		NewServerError(err, s).Abort(c)
+		return
+	}
+	defer handler.Connection.Close()
+
 	// Track this open connection on the server so that we can close them all programmatically
 	// if the server is deleted.
 	s.Websockets().Push(handler.Uuid(), &cancel)
-	defer s.Websockets().Remove(handler.Uuid())
+	handler.Logger().Debug("opening connection to server websocket")
+
+	defer func() {
+		s.Websockets().Remove(handler.Uuid())
+		handler.Logger().Debug("closing connection to server websocket")
+	}()
 
 	// If the server is deleted we need to send a close message to the connected client
 	// so that they disconnect since there will be no more events sent along. Listen for
@@ -57,7 +64,15 @@ func getServerWebsocket(c *gin.Context) {
 		}
 	}()
 
-	go handler.ListenForServerEvents(ctx)
+	go func() {
+		if err := handler.ListenForServerEvents(ctx); err != nil {
+			handler.Logger().Warn("error while processing server event; closing websocket connection")
+			if err := handler.Connection.Close(); err != nil {
+				handler.Logger().WithField("error", errors.WithStack(err)).Error("error closing websocket connection")
+			}
+		}
+	}()
+
 	go handler.ListenForExpiration(ctx)
 
 	for {
@@ -66,7 +81,7 @@ func getServerWebsocket(c *gin.Context) {
 		_, p, err := handler.Connection.ReadMessage()
 		if err != nil {
 			if ws.IsUnexpectedCloseError(err, expectedCloseCodes...) {
-				s.Log().WithField("error", err).Warn("error handling websocket message for server")
+				handler.Logger().WithField("error", err).Warn("error handling websocket message for server")
 			}
 			break
 		}
diff --git a/router/websocket/listeners.go b/router/websocket/listeners.go
index acb762d..21cf859 100644
--- a/router/websocket/listeners.go
+++ b/router/websocket/listeners.go
@@ -2,8 +2,10 @@ package websocket
 
 import (
 	"context"
+	"sync"
 	"time"
 
+	"emperror.dev/errors"
 	"github.com/pterodactyl/wings/events"
 	"github.com/pterodactyl/wings/server"
 )
@@ -52,24 +54,45 @@ var e = []string{
 // ListenForServerEvents will listen for different events happening on a server
 // and send them along to the connected websocket client. This function will
 // block until the context provided to it is canceled.
-func (h *Handler) ListenForServerEvents(ctx context.Context) {
-	h.server.Log().Debug("listening for server events over websocket")
+func (h *Handler) ListenForServerEvents(pctx context.Context) error {
+	var o sync.Once
+	var err error
+	ctx, cancel := context.WithCancel(pctx)
+
+	h.Logger().Debug("listening for server events")
 	callback := func(e events.Event) {
-		if err := h.SendJson(&Message{Event: e.Topic, Args: []string{e.Data}}); err != nil {
-			h.server.Log().WithField("error", err).Warn("error while sending server data over websocket")
+		if sendErr := h.SendJson(&Message{Event: e.Topic, Args: []string{e.Data}}); sendErr != nil {
+			h.Logger().WithField("event", e.Topic).WithField("error", sendErr).Error("failed to send event over server websocket")
+			// Avoid race conditions by only setting the error once and then canceling
+			// the context. This way if additional processing errors come through due
+			// to a massive flood of things you still only report and stop at the first.
+			o.Do(func() {
+				err = sendErr
+				cancel()
+			})
 		}
 	}
 
-	// Subscribe to all of the events with the same callback that will push the data out over the
-	// websocket for the server.
+	// Subscribe to all of the events with the same callback that will push the
+	// data out over the websocket for the server.
 	for _, evt := range e {
 		h.server.Events().On(evt, &callback)
 	}
 
+	// When this function returns de-register all of the event listeners.
+	defer func() {
+		for _, evt := range e {
+			h.server.Events().Off(evt, &callback)
+		}
+	}()
+
 	<-ctx.Done()
-	// Block until the context is stopped and then de-register all of the event listeners
-	// that we registered earlier.
-	for _, evt := range e {
-		h.server.Events().Off(evt, &callback)
+	// If the internal context is stopped it is either because the parent context
+	// got canceled or because we ran into an error. If the "err" variable is nil
+	// we can assume the parent was canceled and need not perform any actions.
+	if err != nil {
+		return errors.WithStack(err)
 	}
+
+	return nil
 }
diff --git a/router/websocket/websocket.go b/router/websocket/websocket.go
index ff5855b..0d37fca 100644
--- a/router/websocket/websocket.go
+++ b/router/websocket/websocket.go
@@ -75,7 +75,7 @@ func NewTokenPayload(token []byte) (*tokens.WebsocketPayload, error) {
 	return &payload, nil
 }
 
-// Returns a new websocket handler using the context provided.
+// GetHandler returns a new websocket handler using the context provided.
 func GetHandler(s *server.Server, w http.ResponseWriter, r *http.Request) (*Handler, error) {
 	upgrader := websocket.Upgrader{
 		// Ensure that the websocket request is originating from the Panel itself,
@@ -116,6 +116,12 @@ func (h *Handler) Uuid() uuid.UUID {
 	return h.uuid
 }
 
+func (h *Handler) Logger() *log.Entry {
+	return log.WithField("subsystem", "websocket").
+		WithField("connection", h.Uuid().String()).
+		WithField("server", h.server.ID())
+}
+
 func (h *Handler) SendJson(v *Message) error {
 	// Do not send JSON down the line if the JWT on the connection is not valid!
 	if err := h.TokenValid(); err != nil {
diff --git a/server/websockets.go b/server/websockets.go
index 981fa79..e86f88c 100644
--- a/server/websockets.go
+++ b/server/websockets.go
@@ -52,8 +52,7 @@ func (w *WebsocketBag) CancelAll() {
 
 	if w.conns != nil {
 		for _, cancel := range w.conns {
-			c := *cancel
-			c()
+			(*cancel)()
 		}
 	}