diff --git a/client/cmd/ssh.go b/client/cmd/ssh.go
index d0f506ff8..dd9407738 100644
--- a/client/cmd/ssh.go
+++ b/client/cmd/ssh.go
@@ -73,7 +73,8 @@ var sshCmd = &cobra.Command{
 		go func() {
 			// blocking
 			if err := runSSH(sshctx, host, []byte(config.SSHKey), cmd); err != nil {
-				log.Print(err)
+				log.Debug(err)
+				os.Exit(1)
 			}
 			cancel()
 		}()
@@ -92,12 +93,10 @@ 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")
-		return nil
+		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 err
 	}
 	go func() {
 		<-ctx.Done()
diff --git a/client/ssh/server.go b/client/ssh/server.go
index 5d63362b9..ae5c65c4a 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"
@@ -13,11 +10,22 @@ 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
 const DefaultSSHPort = 44338
 
+// TerminalTimeout is the timeout for terminal session to be ready
+const TerminalTimeout = 10 * time.Second
+
+// TerminalBackoffDelay is the delay between terminal session readiness checks
+const TerminalBackoffDelay = 500 * time.Millisecond
+
 // DefaultSSHServer is a function that creates DefaultServer
 func DefaultSSHServer(hostKeyPEM []byte, addr string) (Server, error) {
 	return newDefaultServer(hostKeyPEM, addr)
@@ -137,6 +145,8 @@ 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 +182,7 @@ 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)
@@ -199,6 +210,7 @@ func (srv *DefaultServer) sessionHandler(session ssh.Session) {
 			return
 		}
 	}
+	log.Debugf("SSH session ended")
 }
 
 func (srv *DefaultServer) stdInOut(file *os.File, session ssh.Session) {
@@ -206,17 +218,29 @@ func (srv *DefaultServer) stdInOut(file *os.File, session ssh.Session) {
 		// stdin
 		_, err := io.Copy(file, session)
 		if err != nil {
+			_ = session.Exit(1)
 			return
 		}
 	}()
 
-	go func() {
-		// stdout
-		_, err := io.Copy(session, file)
-		if err != nil {
+	// AWS Linux 2 machines need some time to open the terminal so we need to wait for it
+	timer := time.NewTimer(TerminalTimeout)
+	for {
+		select {
+		case <-timer.C:
+			_, _ = session.Write([]byte("Reached timeout while opening connection\n"))
+			_ = session.Exit(1)
 			return
+		default:
+			// stdout
+			writtenBytes, err := io.Copy(session, file)
+			if err != nil && writtenBytes != 0 {
+				_ = session.Exit(0)
+				return
+			}
+			time.Sleep(TerminalBackoffDelay)
 		}
-	}()
+	}
 }
 
 // Start starts SSH server. Blocking