diff --git a/client/cmd/ssh.go b/client/cmd/ssh.go
index d0f506ff8..f97ce5f90 100644
--- a/client/cmd/ssh.go
+++ b/client/cmd/ssh.go
@@ -9,7 +9,6 @@ import (
 	"strings"
 	"syscall"
 
-	log "github.com/sirupsen/logrus"
 	"github.com/spf13/cobra"
 
 	"github.com/netbirdio/netbird/client/internal"
@@ -73,7 +72,8 @@ var sshCmd = &cobra.Command{
 		go func() {
 			// blocking
 			if err := runSSH(sshctx, host, []byte(config.SSHKey), cmd); err != nil {
-				log.Print(err)
+				os.Exit(1)
+				// log.Print(err)
 			}
 			cancel()
 		}()
@@ -92,11 +92,9 @@ func runSSH(ctx context.Context, addr string, pemKey []byte, cmd *cobra.Command)
 	c, err := nbssh.DialWithKey(fmt.Sprintf("%s:%d", addr, port), user, pemKey)
 	if err != nil {
 		cmd.Printf("Error: %v\n", err)
-		cmd.Printf("Couldn't connect. " +
-			"You might be disconnected from the NetBird network, or the NetBird agent isn't running.\n" +
-			"Run the status command: \n\n" +
-			" netbird status\n\n" +
-			"It might also be that the SSH server is disabled on the agent you are trying to connect to.\n")
+		cmd.Printf("Couldn't connect. Please check the connection status or if the ssh server is enabled on the other peer" +
+			"You can verify the connection by running:\n\n" +
+			" netbird status\n\n")
 		return nil
 	}
 	go func() {
diff --git a/client/ssh/server.go b/client/ssh/server.go
index 5d63362b9..f08c5a2f1 100644
--- a/client/ssh/server.go
+++ b/client/ssh/server.go
@@ -2,9 +2,6 @@ package ssh
 
 import (
 	"fmt"
-	"github.com/creack/pty"
-	"github.com/gliderlabs/ssh"
-	log "github.com/sirupsen/logrus"
 	"io"
 	"net"
 	"os"
@@ -13,6 +10,11 @@ import (
 	"runtime"
 	"strings"
 	"sync"
+	"time"
+
+	"github.com/creack/pty"
+	"github.com/gliderlabs/ssh"
+	log "github.com/sirupsen/logrus"
 )
 
 // DefaultSSHPort is the default SSH port of the NetBird's embedded SSH server
@@ -137,6 +139,8 @@ func (srv *DefaultServer) sessionHandler(session ssh.Session) {
 		}
 	}()
 
+	log.Infof("Establishing SSH session for %s from host %s", session.User(), session.RemoteAddr().String())
+
 	localUser, err := userNameLookup(session.User())
 	if err != nil {
 		_, err = fmt.Fprintf(session, "remote SSH server couldn't find local user %s\n", session.User()) //nolint
@@ -172,6 +176,7 @@ func (srv *DefaultServer) sessionHandler(session ssh.Session) {
 			}
 		}
 
+		log.Debugf("Login command: %s", cmd.String())
 		file, err := pty.Start(cmd)
 		if err != nil {
 			log.Errorf("failed starting SSH server %v", err)
@@ -199,24 +204,49 @@ func (srv *DefaultServer) sessionHandler(session ssh.Session) {
 			return
 		}
 	}
+	log.Debugf("SSH session ended")
 }
 
 func (srv *DefaultServer) stdInOut(file *os.File, session ssh.Session) {
 	go func() {
 		// stdin
-		_, err := io.Copy(file, session)
-		if err != nil {
-			return
-		}
+		io.Copy(file, session)
 	}()
 
+	// For nodes on AWS the terminal takes a while to be ready so we need to wait
+	terminalIsReady := make(chan bool)
 	go func() {
-		// stdout
-		_, err := io.Copy(session, file)
-		if err != nil {
-			return
+		for {
+			log.Debugf("Checking if terminal is ready")
+			if checkIfFileIsReady(file) {
+				terminalIsReady <- true
+			}
+			time.Sleep(100 * time.Millisecond)
 		}
 	}()
+	timer := time.NewTimer(30 * time.Second)
+	for {
+		select {
+		case <-timer.C:
+			session.Write([]byte("Reached timeout while opening connection\n"))
+			session.Exit(1)
+		case <-terminalIsReady:
+			// stdout
+			io.Copy(session, file)
+			session.Exit(0)
+		}
+	}
+}
+
+func checkIfFileIsReady(file *os.File) bool {
+	buffer := make([]byte, 0)
+	_, err := file.Read(buffer)
+	// _, err := file.Stat()
+	// log.Infof("file stat: %v", err)
+	if err == nil {
+		return true
+	}
+	return false
 }
 
 // Start starts SSH server. Blocking