diff --git a/web/server.go b/web/server.go
index dfe6ed8..cb1d8f1 100644
--- a/web/server.go
+++ b/web/server.go
@@ -80,10 +80,49 @@ func NewServer(clock *derby.DerbyClock, events <-chan derby.Event, dbPath string
 // routes sets up the routes for the server
 func (s *Server) routes() {
 	// Middleware
+	s.router.Use(middleware.RequestID)
+	s.router.Use(middleware.RealIP)
 	s.router.Use(middleware.Logger)
 	s.router.Use(middleware.Recoverer)
-	// Add timeout middleware with a longer duration for SSE connections
-	s.router.Use(middleware.Timeout(120 * time.Second))
+
+	// Custom middleware to log all requests
+	s.router.Use(func(next http.Handler) http.Handler {
+		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			requestID := middleware.GetReqID(r.Context())
+			s.logger.Info("Request started",
+				"method", r.Method,
+				"path", r.URL.Path,
+				"requestID", requestID,
+				"remoteAddr", r.RemoteAddr)
+
+			start := time.Now()
+			next.ServeHTTP(w, r)
+
+			s.logger.Info("Request completed",
+				"method", r.Method,
+				"path", r.URL.Path,
+				"requestID", requestID,
+				"duration", time.Since(start))
+		})
+	})
+
+	// Use a very long timeout for SSE endpoints, shorter for others
+	s.router.Use(func(next http.Handler) http.Handler {
+		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+			if strings.Contains(r.URL.Path, "/api/events") || strings.Contains(r.URL.Path, "/api/admin/events") {
+				// For SSE endpoints, use a context with a very long timeout
+				ctx, cancel := context.WithTimeout(r.Context(), 24*time.Hour)
+				defer cancel()
+				next.ServeHTTP(w, r.WithContext(ctx))
+			} else {
+				// For regular endpoints, use a shorter timeout
+				ctx, cancel := context.WithTimeout(r.Context(), 30*time.Second)
+				defer cancel()
+				next.ServeHTTP(w, r.WithContext(ctx))
+			}
+		})
+	})
+
 	// Add middleware to set appropriate headers for SSE
 	s.router.Use(func(next http.Handler) http.Handler {
 		return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
@@ -91,6 +130,7 @@ func (s *Server) routes() {
 				w.Header().Set("Cache-Control", "no-cache")
 				w.Header().Set("Connection", "keep-alive")
 				w.Header().Set("Access-Control-Allow-Origin", "*")
+				s.logger.Debug("SSE headers set", "path", r.URL.Path)
 			}
 			next.ServeHTTP(w, r)
 		})
@@ -184,50 +224,76 @@ func (s *Server) Start() error {
 		Addr:    addr,
 		Handler: s.router,
 		// Add these settings to handle multiple concurrent connections
-		ReadTimeout:    30 * time.Second,
-		WriteTimeout:   60 * time.Second, // Longer timeout for SSE connections
-		MaxHeaderBytes: 1 << 20,          // 1 MB
+		ReadTimeout:    120 * time.Second, // Longer timeout for SSE
+		WriteTimeout:   120 * time.Second, // Longer timeout for SSE
 		IdleTimeout:    120 * time.Second,
+		MaxHeaderBytes: 1 << 20, // 1 MB
 	}
 
-	s.logger.Info("Starting web server", "port", s.port)
-	return s.server.ListenAndServe()
-}
+	// Log middleware configuration
+	s.logger.Info("Chi router middleware configuration",
+		"timeout", "120s",
+		"recoverer", true,
+		"logger", true)
 
-// Stop gracefully shuts down the server
-func (s *Server) Stop() error {
-	// Close database connection
-	if s.db != nil {
-		if err := s.db.Close(); err != nil {
-			s.logger.Error("Error closing database", "error", err)
+	// Start server in a goroutine
+	go func() {
+		s.logger.Info("Web server starting", "port", s.port)
+		if err := s.server.ListenAndServe(); err != nil && err != http.ErrServerClosed {
+			s.logger.Error("HTTP server error", "error", err)
 		}
-	}
+	}()
 
-	// Create a context with timeout for shutdown
-	ctx, cancel := context.WithTimeout(context.Background(), 5*time.Second)
-	defer cancel()
+	return nil
+}
 
+// Shutdown gracefully shuts down the server
+func (s *Server) Shutdown(ctx context.Context) error {
 	s.logger.Info("Shutting down web server")
 
-	// Shutdown the HTTP server
-	if s.server != nil {
-		return s.server.Shutdown(ctx)
+	// Signal event forwarder to stop
+	close(s.shutdown)
+
+	// Close all client connections
+	s.clientsMux.Lock()
+	for clientChan := range s.clients {
+		close(clientChan)
 	}
+	s.clients = make(map[chan string]bool)
+	s.clientsMux.Unlock()
 
-	return nil
+	s.adminclientsMux.Lock()
+	for clientChan := range s.adminclients {
+		close(clientChan)
+	}
+	s.adminclients = make(map[chan string]bool)
+	s.adminclientsMux.Unlock()
+
+	// Shutdown the HTTP server
+	return s.server.Shutdown(ctx)
 }
 
 // forwardEvents forwards derby events to SSE clients
 func (s *Server) forwardEvents() {
+	s.logger.Info("Starting event forwarder")
+
 	for {
 		select {
 		case event, ok := <-s.events:
 			if !ok {
+				s.logger.Warn("Events channel closed, stopping forwarder")
 				return
 			}
+
+			s.logger.Debug("Received event from derby clock",
+				"type", event.Type,
+				"clientCount", len(s.clients))
+
 			// Process the event and send to clients
 			s.broadcastRaceEvent(event)
+
 		case <-s.shutdown:
+			s.logger.Info("Shutdown signal received, stopping forwarder")
 			return
 		}
 	}
@@ -316,102 +382,113 @@ func (s *Server) broadcastAdminEvent(event models.AdminEvent) {
 	}
 }
 
+// sendRaceEventToAllClients sends an event to all connected clients
 func (s *Server) sendRaceEventToAllClients(message string) {
-	if message == "" {
-		return
+	// Log the message being sent (truncate if too long)
+	msgToLog := message
+	if len(msgToLog) > 100 {
+		msgToLog = msgToLog[:100] + "..."
 	}
+	s.logger.Debug("Sending message to all clients",
+		"message", msgToLog,
+		"clientCount", len(s.clients))
 
-	// Send to all clients
+	// Make a copy of the clients map to avoid holding the lock while sending
 	s.clientsMux.Lock()
-	clientCount := len(s.clients)
-	sentCount := 0
+	clientsToSend := make([]chan string, 0, len(s.clients))
 	for clientChan := range s.clients {
-		clientChan <- message
-		sentCount++
+		clientsToSend = append(clientsToSend, clientChan)
 	}
-	s.logger.Debug("Event broadcast complete",
-		"sentCount", sentCount,
-		"totalClients", clientCount,
-		"message", message)
 	s.clientsMux.Unlock()
+
+	s.logger.Debug("Prepared to send to clients", "count", len(clientsToSend))
+
+	// Count successful and failed sends
+	successCount := 0
+	failCount := 0
+
+	// Send to all clients without holding the lock
+	for _, clientChan := range clientsToSend {
+		select {
+		case clientChan <- message:
+			// Message sent successfully
+			successCount++
+		default:
+			// Client is not receiving, remove it
+			s.clientsMux.Lock()
+			delete(s.clients, clientChan)
+			s.clientsMux.Unlock()
+			close(clientChan)
+			failCount++
+		}
+	}
+
+	s.logger.Debug("Finished sending message",
+		"successCount", successCount,
+		"failCount", failCount,
+		"remainingClients", len(s.clients))
 }
 
+// sendAdminEventToAllClients sends an event to all connected clients
 func (s *Server) sendAdminEventToAllClients(message string) {
-	if message == "" {
-		return
+	// Log the message being sent (truncate if too long)
+	msgToLog := message
+	if len(msgToLog) > 100 {
+		msgToLog = msgToLog[:100] + "..."
 	}
+	s.logger.Debug("Sending message to all clients",
+		"message", msgToLog,
+		"clientCount", len(s.adminclients))
 
-	// Send to all clients
+	// Make a copy of the clients map to avoid holding the lock while sending
 	s.adminclientsMux.Lock()
-	clientCount := len(s.adminclients)
-	sentCount := 0
+	clientsToSend := make([]chan string, 0, len(s.adminclients))
 	for clientChan := range s.adminclients {
-		clientChan <- message
-		sentCount++
+		clientsToSend = append(clientsToSend, clientChan)
 	}
-	s.logger.Debug("Event broadcast complete",
-		"sentCount", sentCount,
-		"totalClients", clientCount,
-		"message", message)
 	s.adminclientsMux.Unlock()
-}
 
-// handleIndex handles the index page
-func (s *Server) handleIndex() http.HandlerFunc {
-	return func(w http.ResponseWriter, r *http.Request) {
-		templates.Index().Render(r.Context(), w)
-	}
-}
+	s.logger.Debug("Prepared to send to clients", "count", len(clientsToSend))
 
-// handleReset handles the reset API endpoint
-func (s *Server) handleReset() http.HandlerFunc {
-	return func(w http.ResponseWriter, r *http.Request) {
-		if err := s.clock.Reset(); err != nil {
-			http.Error(w, fmt.Sprintf("Failed to reset clock: %v", err), http.StatusInternalServerError)
-			return
-		}
-
-		w.Header().Set("Content-Type", "application/json")
-		w.Write([]byte(`{"status": "reset"}`))
-	}
-}
+	// Count successful and failed sends
+	successCount := 0
+	failCount := 0
 
-// handleForceEnd handles the force end API endpoint
-func (s *Server) handleForceEnd() http.HandlerFunc {
-	return func(w http.ResponseWriter, r *http.Request) {
-		if err := s.clock.ForceEnd(); err != nil {
-			http.Error(w, fmt.Sprintf("Failed to force end race: %v", err), http.StatusInternalServerError)
-			return
+	// Send to all clients without holding the lock
+	for _, clientChan := range clientsToSend {
+		select {
+		case clientChan <- message:
+			// Message sent successfully
+			successCount++
+		default:
+			// Client is not receiving, remove it
+			s.adminclientsMux.Lock()
+			delete(s.adminclients, clientChan)
+			s.adminclientsMux.Unlock()
+			close(clientChan)
+			failCount++
 		}
-
-		w.Header().Set("Content-Type", "application/json")
-		w.Write([]byte(`{"status": "forced"}`))
 	}
-}
 
-// handleStatus handles the status API endpoint
-func (s *Server) handleStatus() http.HandlerFunc {
-	return func(w http.ResponseWriter, r *http.Request) {
-		status := s.clock.Status()
-
-		var statusStr string
-		switch status {
-		case derby.StatusIdle:
-			statusStr = "idle"
-		case derby.StatusRunning:
-			statusStr = "running"
-		case derby.StatusFinished:
-			statusStr = "finished"
-		}
-
-		w.Header().Set("Content-Type", "application/json")
-		w.Write([]byte(fmt.Sprintf(`{"status": "%s"}`, statusStr)))
-	}
+	s.logger.Debug("Finished sending message",
+		"successCount", successCount,
+		"failCount", failCount,
+		"remainingClients", len(s.adminclients))
 }
 
 // handleEvents handles SSE events
 func (s *Server) handleEvents() http.HandlerFunc {
 	return func(w http.ResponseWriter, r *http.Request) {
+		requestID := middleware.GetReqID(r.Context())
+		if requestID == "" {
+			requestID = fmt.Sprintf("req-%d", time.Now().UnixNano())
+		}
+
+		s.logger.Info("SSE connection request received",
+			"requestID", requestID,
+			"remoteAddr", r.RemoteAddr,
+			"userAgent", r.UserAgent())
+
 		// Set headers for SSE
 		w.Header().Set("Content-Type", "text/event-stream")
 		w.Header().Set("Cache-Control", "no-cache")
@@ -420,8 +497,10 @@ func (s *Server) handleEvents() http.HandlerFunc {
 
 		// Flush headers to ensure they're sent to the client
 		if flusher, ok := w.(http.Flusher); ok {
+			s.logger.Debug("Flushing headers", "requestID", requestID)
 			flusher.Flush()
 		} else {
+			s.logger.Error("Streaming unsupported!", "requestID", requestID)
 			http.Error(w, "Streaming unsupported!", http.StatusInternalServerError)
 			return
 		}
@@ -436,9 +515,18 @@ func (s *Server) handleEvents() http.HandlerFunc {
 		s.clientsMux.Unlock()
 
 		s.logger.Info("New client connected",
+			"requestID", requestID,
 			"clientIP", r.RemoteAddr,
 			"totalClients", clientCount)
 
+		// Send a ping immediately to test the connection
+		pingMsg := "event: ping\ndata: connection established\n\n"
+		fmt.Fprint(w, pingMsg)
+		if flusher, ok := w.(http.Flusher); ok {
+			flusher.Flush()
+			s.logger.Debug("Initial ping sent", "requestID", requestID)
+		}
+
 		// Remove client when connection is closed
 		defer func() {
 			s.clientsMux.Lock()
@@ -448,28 +536,107 @@ func (s *Server) handleEvents() http.HandlerFunc {
 			close(clientChan)
 
 			s.logger.Info("Client disconnected",
+				"requestID", requestID,
 				"clientIP", r.RemoteAddr,
 				"remainingClients", remainingClients)
 		}()
 
+		// Set up a heartbeat to keep the connection alive
+		heartbeat := time.NewTicker(30 * time.Second)
+		defer heartbeat.Stop()
+
 		// Keep connection open and send events as they arrive
 		for {
 			select {
 			case msg, ok := <-clientChan:
 				if !ok {
+					s.logger.Warn("Client channel closed", "requestID", requestID)
 					return
 				}
-				fmt.Fprintf(w, "%s\n\n", msg)
+
+				s.logger.Debug("Sending message to client",
+					"requestID", requestID,
+					"messageLength", len(msg))
+
+				fmt.Fprint(w, msg)
 				if flusher, ok := w.(http.Flusher); ok {
 					flusher.Flush()
+					s.logger.Debug("Message flushed", "requestID", requestID)
+				} else {
+					s.logger.Warn("Could not flush - client may not receive updates", "requestID", requestID)
 				}
+
+			case <-heartbeat.C:
+				// Send a heartbeat to keep the connection alive
+				s.logger.Debug("Sending heartbeat", "requestID", requestID)
+				fmt.Fprint(w, "event: ping\ndata: heartbeat\n\n")
+				if flusher, ok := w.(http.Flusher); ok {
+					flusher.Flush()
+				}
+
 			case <-r.Context().Done():
+				s.logger.Info("Client context done",
+					"requestID", requestID,
+					"error", r.Context().Err())
 				return
 			}
 		}
 	}
 }
 
+// handleIndex handles the index page
+func (s *Server) handleIndex() http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		templates.Index().Render(r.Context(), w)
+	}
+}
+
+// handleReset handles the reset API endpoint
+func (s *Server) handleReset() http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		if err := s.clock.Reset(); err != nil {
+			http.Error(w, fmt.Sprintf("Failed to reset clock: %v", err), http.StatusInternalServerError)
+			return
+		}
+
+		w.Header().Set("Content-Type", "application/json")
+		w.Write([]byte(`{"status": "reset"}`))
+	}
+}
+
+// handleForceEnd handles the force end API endpoint
+func (s *Server) handleForceEnd() http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		if err := s.clock.ForceEnd(); err != nil {
+			http.Error(w, fmt.Sprintf("Failed to force end race: %v", err), http.StatusInternalServerError)
+			return
+		}
+
+		w.Header().Set("Content-Type", "application/json")
+		w.Write([]byte(`{"status": "forced"}`))
+	}
+}
+
+// handleStatus handles the status API endpoint
+func (s *Server) handleStatus() http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		status := s.clock.Status()
+
+		var statusStr string
+		switch status {
+		case derby.StatusIdle:
+			statusStr = "idle"
+		case derby.StatusRunning:
+			statusStr = "running"
+		case derby.StatusFinished:
+			statusStr = "finished"
+		}
+
+		w.Header().Set("Content-Type", "application/json")
+		w.Write([]byte(fmt.Sprintf(`{"status": "%s"}`, statusStr)))
+	}
+}
+
 // handleAdminEvents handles SSE events
 func (s *Server) handleAdminEvents() http.HandlerFunc {
 	return func(w http.ResponseWriter, r *http.Request) {