diff --git a/arduino/monitor/monitor.go b/arduino/monitor/monitor.go
index 76eeb232dd0..4e53435ebc7 100644
--- a/arduino/monitor/monitor.go
+++ b/arduino/monitor/monitor.go
@@ -103,24 +103,23 @@ func (mon *PluggableMonitor) String() string {
 	return mon.id
 }
 
-func (mon *PluggableMonitor) jsonDecodeLoop(in io.Reader, outChan chan<- *monitorMessage) {
+func jsonDecodeLoop(in io.Reader, outChan chan<- *monitorMessage, log *logrus.Entry, lastError *error) {
 	decoder := json.NewDecoder(in)
 
 	for {
 		var msg monitorMessage
 		if err := decoder.Decode(&msg); err != nil {
-			mon.incomingMessagesError = err
+			*lastError = err
 			close(outChan)
-			mon.log.Errorf("stopped decode loop: %s", err)
+			log.Errorf("stopped decode loop: %s", err)
 			return
 		}
-		mon.log.
-			WithField("event_type", msg.EventType).
+		log.WithField("event_type", msg.EventType).
 			WithField("message", msg.Message).
 			WithField("error", msg.Error).
 			Infof("received message")
 		if msg.EventType == "port_closed" {
-			mon.log.Infof("monitor port has been closed externally")
+			log.Infof("monitor port has been closed externally")
 		} else {
 			outChan <- &msg
 		}
@@ -128,13 +127,15 @@ func (mon *PluggableMonitor) jsonDecodeLoop(in io.Reader, outChan chan<- *monito
 }
 
 func (mon *PluggableMonitor) waitMessage(timeout time.Duration, expectedEvt string) (*monitorMessage, error) {
+	mon.log.WithField("expected", expectedEvt).Debugf("waiting for event")
 	var msg *monitorMessage
 	select {
-	case msg = <-mon.incomingMessagesChan:
-		if msg == nil {
+	case m, ok := <-mon.incomingMessagesChan:
+		if !ok {
 			// channel has been closed
 			return nil, mon.incomingMessagesError
 		}
+		msg = m
 	case <-time.After(timeout):
 		return nil, fmt.Errorf(tr("timeout waiting for message"))
 	}
@@ -192,22 +193,21 @@ func (mon *PluggableMonitor) runProcess() error {
 
 	messageChan := make(chan *monitorMessage)
 	mon.incomingMessagesChan = messageChan
-	go mon.jsonDecodeLoop(stdout, messageChan)
+	go jsonDecodeLoop(stdout, messageChan, mon.log, &mon.incomingMessagesError)
 
 	mon.log.Infof("Monitor process started successfully!")
 	return nil
 }
 
-func (mon *PluggableMonitor) killProcess() error {
+func (mon *PluggableMonitor) killProcess() {
 	mon.log.Infof("Killing monitor process")
 	if err := mon.process.Kill(); err != nil {
-		return err
+		mon.log.WithError(err).Error("Sent kill signal")
 	}
 	if err := mon.process.Wait(); err != nil {
-		return err
+		mon.log.WithError(err).Error("Waiting for process end")
 	}
-	mon.log.Infof("Monitor process killed successfully!")
-	return nil
+	mon.log.Infof("Monitor process killed")
 }
 
 // Run starts the monitor executable process and sends the HELLO command to the monitor to agree on the
@@ -220,15 +220,10 @@ func (mon *PluggableMonitor) Run() (err error) {
 
 	defer func() {
 		// If the monitor process is started successfully but the HELLO handshake
-		// fails the monitor is an unusable state, we kill the process to avoid
+		// fails the monitor is in an unusable state, we kill the process to avoid
 		// further issues down the line.
-		if err == nil {
-			return
-		}
-		if killErr := mon.killProcess(); killErr != nil {
-			// Log failure to kill the process, ideally that should never happen
-			// but it's best to know it if it does
-			mon.log.Errorf("Killing monitor after unsuccessful start: %s", killErr)
+		if err != nil {
+			mon.killProcess()
 		}
 	}()
 
@@ -297,20 +292,19 @@ func (mon *PluggableMonitor) Close() error {
 	if err := mon.sendCommand("CLOSE\n"); err != nil {
 		return err
 	}
-	_, err := mon.waitMessage(time.Second*10, "close")
+	_, err := mon.waitMessage(time.Millisecond*250, "close")
 	return err
 }
 
 // Quit terminates the monitor. No more commands can be accepted by the monitor.
 func (mon *PluggableMonitor) Quit() error {
+	defer mon.killProcess() // ensure that killProcess is called in any case...
+
 	if err := mon.sendCommand("QUIT\n"); err != nil {
 		return err
 	}
-	if _, err := mon.waitMessage(time.Second*10, "quit"); err != nil {
+	if _, err := mon.waitMessage(time.Millisecond*250, "quit"); err != nil {
 		return err
 	}
-	if err := mon.killProcess(); err != nil {
-		mon.log.WithError(err).Info("error killing monitor process")
-	}
 	return nil
 }
diff --git a/commands/daemon/daemon.go b/commands/daemon/daemon.go
index 6748e48c284..9c442070523 100644
--- a/commands/daemon/daemon.go
+++ b/commands/daemon/daemon.go
@@ -508,9 +508,11 @@ func (s *ArduinoCoreServerImpl) Monitor(stream rpc.ArduinoCoreService_MonitorSer
 	if err != nil {
 		return err
 	}
-	ctx, cancel := context.WithCancel(stream.Context())
+
 	go func() {
-		defer cancel()
+		// close port on gRPC call EOF or errors
+		defer portProxy.Close()
+
 		for {
 			msg, err := stream.Recv()
 			if errors.Is(err, io.EOF) {
@@ -541,23 +543,20 @@ func (s *ArduinoCoreServerImpl) Monitor(stream rpc.ArduinoCoreService_MonitorSer
 			}
 		}
 	}()
-	go func() {
-		defer cancel()
-		buff := make([]byte, 4096)
-		for {
-			n, err := portProxy.Read(buff)
-			if errors.Is(err, io.EOF) {
-				return
-			}
-			if err != nil {
-				stream.Send(&rpc.MonitorResponse{Error: err.Error()})
-				return
-			}
-			if err := stream.Send(&rpc.MonitorResponse{RxData: buff[:n]}); err != nil {
-				return
-			}
+
+	buff := make([]byte, 4096)
+	for {
+		n, err := portProxy.Read(buff)
+		if errors.Is(err, io.EOF) {
+			break
 		}
-	}()
-	<-ctx.Done()
+		if err != nil {
+			stream.Send(&rpc.MonitorResponse{Error: err.Error()})
+			break
+		}
+		if err := stream.Send(&rpc.MonitorResponse{RxData: buff[:n]}); err != nil {
+			break
+		}
+	}
 	return nil
 }
diff --git a/commands/daemon/term_example/main.go b/commands/daemon/term_example/main.go
index 4b9227c5a75..0326e052871 100644
--- a/commands/daemon/term_example/main.go
+++ b/commands/daemon/term_example/main.go
@@ -74,52 +74,54 @@ func main() {
 	}
 	fmt.Println("Detected port:", port.Label, port.ProtocolLabel)
 
+	connectToPort(cli, instance, port)
+	time.Sleep(5 * time.Second)
+	connectToPort(cli, instance, port)
+	time.Sleep(5 * time.Second)
+}
+
+func connectToPort(cli commands.ArduinoCoreServiceClient, instance *commands.Instance, port *commands.Port) {
 	// Connect to the port monitor
-	fmt.Println("Connecting to monitor")
+	fmt.Println("Connecting to port", port)
+
 	ctx, cancel := context.WithCancel(context.Background())
-	if respStream, err := cli.Monitor(ctx); err != nil {
-		log.Fatal("Monitor:", err)
-	} else {
-		if err := respStream.Send(&commands.MonitorRequest{
-			Instance: instance,
-			Port:     port,
-		}); err != nil {
-			log.Fatal("Monitor send-config:", err)
-		}
-		time.Sleep(1 * time.Second)
-
-		go func() {
-			for {
-				if resp, err := respStream.Recv(); err != nil {
-					fmt.Println("     RECV:", err)
-					break
-				} else {
-					fmt.Println("     RECV:", resp)
-				}
-			}
-		}()
+	monitorClient, err := cli.Monitor(ctx)
+	if err != nil {
+		log.Fatal("Error opening Monitor:", err)
+	}
+	if err := monitorClient.Send(&commands.MonitorRequest{
+		Instance: instance,
+		Port:     port,
+	}); err != nil {
+		log.Fatal("Error sending Monitor config:", err)
+	}
 
-		hello := &commands.MonitorRequest{
-			TxData: []byte("HELLO!"),
-		}
-		fmt.Println("Send:", hello)
-		if err := respStream.Send(hello); err != nil {
-			log.Fatal("Monitor send HELLO:", err)
+	go func() {
+		for {
+			resp, err := monitorClient.Recv()
+			if err != nil {
+				fmt.Println("     RECV-ERR:", err)
+				break
+			}
+			fmt.Println("     RECV:", resp)
 		}
+	}()
 
-		fmt.Println("Send:", hello)
-		if err := respStream.Send(hello); err != nil {
-			log.Fatal("Monitor send HELLO:", err)
-		}
+	hello := &commands.MonitorRequest{
+		TxData: []byte("HELLO!"),
+	}
+	fmt.Println("Send:", hello)
+	if err := monitorClient.Send(hello); err != nil {
+		log.Fatal("Monitor send HELLO:", err)
+	}
 
-		time.Sleep(5 * time.Second)
+	time.Sleep(15 * time.Second)
 
-		fmt.Println("Closing Monitor")
-		if err := respStream.CloseSend(); err != nil {
-			log.Fatal("Monitor close send:", err)
-		}
-		time.Sleep(5 * time.Second)
+	fmt.Println("Closing Monitor")
+	if err := monitorClient.CloseSend(); err != nil {
+		log.Fatal("Monitor close send:", err)
 	}
+	<-monitorClient.Context().Done()
+
 	cancel()
-	time.Sleep(5 * time.Second)
 }
diff --git a/commands/monitor/monitor.go b/commands/monitor/monitor.go
index 3d2995a6b59..6690621ffab 100644
--- a/commands/monitor/monitor.go
+++ b/commands/monitor/monitor.go
@@ -86,10 +86,11 @@ func Monitor(ctx context.Context, req *rpc.MonitorRequest) (*PortProxy, *pluggab
 		m.Quit()
 		return nil, nil, &arduino.FailedMonitorError{Cause: err}
 	}
-
-	for _, setting := range req.GetPortConfiguration().Settings {
-		if err := m.Configure(setting.SettingId, setting.Value); err != nil {
-			logrus.Errorf("Could not set configuration %s=%s: %s", setting.SettingId, setting.Value, err)
+	if portConfig := req.GetPortConfiguration(); portConfig != nil {
+		for _, setting := range portConfig.Settings {
+			if err := m.Configure(setting.SettingId, setting.Value); err != nil {
+				logrus.Errorf("Could not set configuration %s=%s: %s", setting.SettingId, setting.Value, err)
+			}
 		}
 	}