diff --git a/gateway/nginx/conf.d/shellhub.conf b/gateway/nginx/conf.d/shellhub.conf
index fd8b68c0970..1c4b58bcca4 100644
--- a/gateway/nginx/conf.d/shellhub.conf
+++ b/gateway/nginx/conf.d/shellhub.conf
@@ -258,6 +258,7 @@ server {
         {{ end -}}
         proxy_set_header X-Device-UID $device_uid;
         proxy_set_header X-Tenant-ID $tenant_id;
+        proxy_set_header X-Request-ID $request_id;
         proxy_http_version 1.1;
         proxy_cache_bypass $http_upgrade;
         proxy_redirect off;
diff --git a/pkg/connman/connman.go b/pkg/connman/connman.go
index fbc6c8a799d..bf30e5faae2 100644
--- a/pkg/connman/connman.go
+++ b/pkg/connman/connman.go
@@ -4,10 +4,12 @@ import (
 	"context"
 	"errors"
 	"net"
+	"os"
+	"strings"
 
 	"github.com/shellhub-io/shellhub/pkg/revdial"
 	"github.com/shellhub-io/shellhub/pkg/wsconnadapter"
-	"github.com/sirupsen/logrus"
+	log "github.com/sirupsen/logrus"
 )
 
 var ErrNoConnection = errors.New("no connection")
@@ -27,12 +29,23 @@ func New() *ConnectionManager {
 }
 
 func (m *ConnectionManager) Set(key string, conn *wsconnadapter.Adapter, connPath string) {
-	dialer := revdial.NewDialer(conn, connPath)
+	parts := strings.Split(key, ":")
+	logger := (&log.Logger{
+		Out:       os.Stderr,
+		Formatter: log.StandardLogger().Formatter,
+		Hooks:     log.StandardLogger().Hooks,
+		Level:     log.StandardLogger().Level,
+	}).WithFields(log.Fields{
+		"tenant": parts[0],
+		"device": parts[1],
+	})
+
+	dialer := revdial.NewDialer(logger, conn, connPath)
 
 	m.dialers.Store(key, dialer)
 
 	if size := m.dialers.Size(key); size > 1 {
-		logrus.WithFields(logrus.Fields{
+		log.WithFields(log.Fields{
 			"key":  key,
 			"size": size,
 		}).Warning("Multiple connections stored for the same identifier.")
@@ -67,7 +80,7 @@ func (m *ConnectionManager) Dial(ctx context.Context, key string) (net.Conn, err
 	}
 
 	if size := m.dialers.Size(key); size > 1 {
-		logrus.WithFields(logrus.Fields{
+		log.WithFields(log.Fields{
 			"key":  key,
 			"size": size,
 		}).Warning("Multiple connections found for the same identifier during reverse tunnel dialing.")
diff --git a/pkg/httptunnel/httptunnel.go b/pkg/httptunnel/httptunnel.go
index a597bfaafa5..af2996c98cc 100644
--- a/pkg/httptunnel/httptunnel.go
+++ b/pkg/httptunnel/httptunnel.go
@@ -6,12 +6,14 @@ import (
 	"io"
 	"net"
 	"net/http"
+	"strings"
 
 	"github.com/gorilla/websocket"
 	"github.com/labstack/echo/v4"
 	"github.com/shellhub-io/shellhub/pkg/connman"
 	"github.com/shellhub-io/shellhub/pkg/revdial"
 	"github.com/shellhub-io/shellhub/pkg/wsconnadapter"
+	log "github.com/sirupsen/logrus"
 )
 
 var upgrader = websocket.Upgrader{
@@ -75,14 +77,21 @@ func (t *Tunnel) Router() http.Handler {
 			return c.String(http.StatusInternalServerError, err.Error())
 		}
 
-		id, err := t.ConnectionHandler(c.Request())
+		key, err := t.ConnectionHandler(c.Request())
 		if err != nil {
 			conn.Close()
 
 			return c.String(http.StatusBadRequest, err.Error())
 		}
 
-		t.connman.Set(id, wsconnadapter.New(conn), t.DialerPath)
+		parts := strings.Split(key, ":")
+		log.WithFields(log.Fields{
+			"request-id": c.Request().Header.Get("X-Request-ID"),
+			"tenant":     parts[0],
+			"device":     parts[1],
+		}).Debug("new ssh connection")
+
+		t.connman.Set(key, wsconnadapter.New(conn), t.DialerPath)
 
 		return nil
 	})
diff --git a/pkg/revdial/revdial.go b/pkg/revdial/revdial.go
index 39fe0911194..41277e00adf 100644
--- a/pkg/revdial/revdial.go
+++ b/pkg/revdial/revdial.go
@@ -24,7 +24,6 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
-	"log"
 	"net"
 	"net/http"
 	"strings"
@@ -34,11 +33,13 @@ import (
 	"github.com/gorilla/websocket"
 	"github.com/shellhub-io/shellhub/pkg/clock"
 	"github.com/shellhub-io/shellhub/pkg/wsconnadapter"
-	"github.com/sirupsen/logrus"
+	log "github.com/sirupsen/logrus"
 )
 
-var ErrDialerClosed = errors.New("revdial.Dialer closed")
-var ErrDialerTimedout = errors.New("revdial.Dialer timedout")
+var (
+	ErrDialerClosed   = errors.New("revdial.Dialer closed")
+	ErrDialerTimedout = errors.New("revdial.Dialer timedout")
+)
 
 // dialerUniqParam is the parameter name of the GET URL form value
 // containing the Dialer's random unique ID.
@@ -59,11 +60,10 @@ type Dialer struct {
 	connReady    chan bool
 	donec        chan struct{}
 	closeOnce    sync.Once
+	logger       *log.Entry
 }
 
-var (
-	dialers = sync.Map{}
-)
+var dialers = sync.Map{}
 
 // NewDialer returns the side of the connection which will initiate
 // new connections. This will typically be the side which did the HTTP
@@ -71,7 +71,7 @@ var (
 // connection. The connPath is the HTTP path and optional query (but
 // without scheme or host) on the dialer where the ConnHandler is
 // mounted.
-func NewDialer(c net.Conn, connPath string) *Dialer {
+func NewDialer(logger *log.Entry, c net.Conn, connPath string) *Dialer {
 	d := &Dialer{
 		path:         connPath,
 		uniqID:       newUniqID(),
@@ -80,6 +80,7 @@ func NewDialer(c net.Conn, connPath string) *Dialer {
 		connReady:    make(chan bool),
 		incomingConn: make(chan net.Conn),
 		pickupFailed: make(chan error),
+		logger:       logger,
 	}
 
 	join := "?"
@@ -121,6 +122,8 @@ func (d *Dialer) Close() error {
 }
 
 func (d *Dialer) close() {
+	d.logger.Debug("dialer connection closed")
+
 	d.unregister()
 	d.conn.Close()
 	d.donec <- struct{}{}
@@ -165,21 +168,24 @@ func (d *Dialer) serve() error {
 
 	go func() {
 		defer d.Close()
+		defer d.logger.Debug("dialer serve done due reader error")
 
 		br := bufio.NewReader(d.conn)
 		for {
 			line, err := br.ReadSlice('\n')
 			if err != nil {
+				d.logger.WithError(err).Debug("failed to read the agent's command")
+
 				unexpectedError := websocket.IsUnexpectedCloseError(err, websocket.CloseGoingAway, websocket.CloseAbnormalClosure)
 				if !errors.Is(err, net.ErrClosed) && unexpectedError {
-					logrus.WithError(err).Error("revdial.Dialer failed to read")
+					d.logger.WithError(err).Error("revdial.Dialer failed to read")
 				}
 
 				return
 			}
 			var msg controlMsg
 			if err := json.Unmarshal(line, &msg); err != nil {
-				log.Printf("revdial.Dialer read invalid JSON: %q: %v", line, err)
+				d.logger.Printf("revdial.Dialer read invalid JSON: %q: %v", line, err)
 
 				return
 			}
@@ -190,16 +196,21 @@ func (d *Dialer) serve() error {
 				select {
 				case d.pickupFailed <- err:
 				case <-d.donec:
+					d.logger.WithError(err).Debug("failed to pick-up connection")
+
 					return
 				}
 			case "keep-alive":
 			default:
 				// Ignore unknown messages
+				log.WithField("message", msg.Command).Debug("unknown message received")
 			}
 		}
 	}()
 	for {
 		if err := d.sendMessage(controlMsg{Command: "keep-alive"}); err != nil {
+			d.logger.WithError(err).Debug("failed to send keep-alive message to device")
+
 			return err
 		}
 
@@ -213,6 +224,8 @@ func (d *Dialer) serve() error {
 				Command:  "conn-ready",
 				ConnPath: d.pickupPath,
 			}); err != nil {
+				d.logger.WithError(err).Debug("failed to send conn-ready message to device")
+
 				return err
 			}
 		case <-d.donec:
@@ -225,6 +238,8 @@ func (d *Dialer) serve() error {
 
 func (d *Dialer) sendMessage(m controlMsg) error {
 	if err := d.conn.SetWriteDeadline(clock.Now().Add(10 * time.Second)); err != nil {
+		d.logger.WithError(err).Debug("failed to set the write dead line to device")
+
 		return err
 	}
 
@@ -232,6 +247,8 @@ func (d *Dialer) sendMessage(m controlMsg) error {
 	j = append(j, '\n')
 
 	if _, err := d.conn.Write(j); err != nil {
+		d.logger.WithError(err).Debug("failed to write on the connection")
+
 		return err
 	}
 
diff --git a/pkg/wsconnadapter/wsconnadapter.go b/pkg/wsconnadapter/wsconnadapter.go
index 19ab06b57ca..0b9a0d2605c 100644
--- a/pkg/wsconnadapter/wsconnadapter.go
+++ b/pkg/wsconnadapter/wsconnadapter.go
@@ -8,7 +8,7 @@ import (
 	"time"
 
 	"github.com/gorilla/websocket"
-	"github.com/sirupsen/logrus"
+	log "github.com/sirupsen/logrus"
 )
 
 // an adapter for representing WebSocket connection as a net.Conn
@@ -71,9 +71,11 @@ func (a *Adapter) Ping() chan bool {
 			select {
 			case <-ticker.C:
 				if err := a.conn.WriteControl(websocket.PingMessage, []byte{}, time.Now().Add(5*time.Second)); err != nil {
-					logrus.WithError(err).Error("Failed to write ping message")
+					log.WithError(err).Error("Failed to write ping message")
 				}
 			case <-a.stopPingCh:
+				log.Debug("Stop ping message received")
+
 				return
 			}
 		}