Thanks to a tweet Dominic responded to, I saw someone mention Passing-the-hash when I think they actually meant relay. The terminology can be confusing for sure, however, it made me realise that I had never Passed-the-hash with a Wi-Fi network. So having learnt my lesson from previous projects I first made sure this was possible for NT -> MSCHAP by looking at the RFC. 8.1. GenerateNTResponse() GenerateNTResponse( IN 16-octet AuthenticatorChallenge, IN 16-octet PeerChallenge, IN 0-to-256-char UserName, IN 0-to-256-unicode-char Password, OUT 24-octet Response ) { 8-octet Challenge 16-octet PasswordHash ChallengeHash( PeerChallenge, AuthenticatorChallenge, UserName, giving Challenge) NtPasswordHash( Password, giving PasswordHash ) ChallengeResponse( Challenge, PasswordHash, giving Response ) } Looks like you can! As you can see in the above, the ChallengeResponse is created using the NT hash and not the password. I then checked wpa_supplicant to see if this was not a feature already, and it turns out it is! Looking at the wpa_supplicant configuration file it says: