MikroTik WinBox 3.22 and below stores the user's cleartext password in the settings.cfg.viw configuration file when the Keep Password field is set and no Master Password is set. Keep Password is set by default and, by default Master Password is not set. An attacker with access to the configuration file can extract a username and password to gain access to the router.

MikroTik WinBox before 3.21 is vulnerable to a path traversal vulnerability that allows creation of arbitrary files wherevere WinBox has write permissions. WinBox is vulnerable to this attack if it connects to a malicious endpoint or if an attacker mounts a man in the middle attack.

MikroTik Winbox 3.20 and below is vulnerable to man in the middle attacks. A man in the middle can downgrade the client's authentication protocol and recover the user's username and MD5 hashed password.