diff --git a/application/commands/ssh.go b/application/commands/ssh.go
index 5910aaf..756f0e4 100644
--- a/application/commands/ssh.go
+++ b/application/commands/ssh.go
@@ -111,6 +111,7 @@ type sshRemoteConnWrapper struct {
 
 	readTimeout   time.Duration
 	enableTimeout bool
+	retryTimeout  func() bool
 }
 
 func (s *sshRemoteConnWrapper) SetReadDeadline(t time.Time) error {
@@ -150,7 +151,25 @@ func (s *sshRemoteConnWrapper) Read(b []byte) (int, error) {
 
 	s.Conn.SetReadDeadline(time.Now().Add(s.readTimeout))
 
-	return s.Conn.Read(b)
+	for {
+		rLen, rErr := s.Conn.Read(b)
+
+		if rErr == nil {
+			return rLen, nil
+		}
+
+		if !s.enableTimeout {
+			return rLen, rErr
+		}
+
+		netErr, isNetErr := rErr.(net.Error)
+
+		if !isNetErr || !netErr.Timeout() || !s.retryTimeout() {
+			return rLen, rErr
+		}
+
+		s.Conn.SetReadDeadline(time.Now().Add(s.readTimeout))
+	}
 }
 
 type sshRemoteConn struct {
@@ -168,6 +187,8 @@ type sshClient struct {
 	l                                    log.Logger
 	cfg                                  command.Configuration
 	remoteCloseWait                      sync.WaitGroup
+	remoteReadTimeoutRetry               bool
+	remoteReadTimeoutRetryLock           sync.Mutex
 	credentialReceive                    chan []byte
 	credentialProcessed                  bool
 	credentialReceiveClosed              bool
@@ -188,6 +209,8 @@ func newSSH(
 		l:                                    l,
 		cfg:                                  cfg,
 		remoteCloseWait:                      sync.WaitGroup{},
+		remoteReadTimeoutRetry:               false,
+		remoteReadTimeoutRetryLock:           sync.Mutex{},
 		credentialReceive:                    make(chan []byte, 1),
 		credentialProcessed:                  false,
 		credentialReceiveClosed:              false,
@@ -261,6 +284,9 @@ func (d *sshClient) buildAuthMethod(
 		return func(b []byte) []ssh.AuthMethod {
 			return []ssh.AuthMethod{
 				ssh.PasswordCallback(func() (string, error) {
+					d.enableRemoteReadTimeoutRetry()
+					defer d.disableRemoteReadTimeoutRetry()
+
 					wErr := d.w.SendManual(
 						SSHServerConnectRequestCredential,
 						b[d.w.HeaderSize():],
@@ -285,6 +311,9 @@ func (d *sshClient) buildAuthMethod(
 		return func(b []byte) []ssh.AuthMethod {
 			return []ssh.AuthMethod{
 				ssh.PublicKeysCallback(func() ([]ssh.Signer, error) {
+					d.enableRemoteReadTimeoutRetry()
+					defer d.disableRemoteReadTimeoutRetry()
+
 					wErr := d.w.SendManual(
 						SSHServerConnectRequestCredential,
 						b[d.w.HeaderSize():],
@@ -321,6 +350,9 @@ func (d *sshClient) comfirmRemoteFingerprint(
 	key ssh.PublicKey,
 	buf []byte,
 ) error {
+	d.enableRemoteReadTimeoutRetry()
+	defer d.disableRemoteReadTimeoutRetry()
+
 	fgp := ssh.FingerprintSHA256(key)
 	fgpLen := copy(buf[d.w.HeaderSize():], fgp)
 
@@ -346,6 +378,20 @@ func (d *sshClient) comfirmRemoteFingerprint(
 	return nil
 }
 
+func (d *sshClient) enableRemoteReadTimeoutRetry() {
+	d.remoteReadTimeoutRetryLock.Lock()
+	defer d.remoteReadTimeoutRetryLock.Unlock()
+
+	d.remoteReadTimeoutRetry = true
+}
+
+func (d *sshClient) disableRemoteReadTimeoutRetry() {
+	d.remoteReadTimeoutRetryLock.Lock()
+	defer d.remoteReadTimeoutRetryLock.Unlock()
+
+	d.remoteReadTimeoutRetry = false
+}
+
 func (d *sshClient) dialRemote(
 	network,
 	addr string,
@@ -362,6 +408,12 @@ func (d *sshClient) dialRemote(
 		Conn:          conn,
 		readTimeout:   config.Timeout,
 		enableTimeout: true,
+		retryTimeout: func() bool {
+			d.remoteReadTimeoutRetryLock.Lock()
+			defer d.remoteReadTimeoutRetryLock.Unlock()
+
+			return d.remoteReadTimeoutRetry
+		},
 	}
 
 	c, chans, reqs, err := ssh.NewClientConn(&sshConn, addr, config)