It seems that I have ntlm_auth configured to talk to Samba correctly. As it positively works when run from the CLI and FR even shows a positive login, but that positive login never seems to be sent to the authentication stage. More food for thought once I tackle this, is that when I try to link all this together with a Netgear WAP, plain-text users in the users file works perfectly fine. Log output: rad_recv: Access-Request packet from host 127.0.0.1 port 35826, id=114, length=57 User-Name = "wyse1" User-Password = "K503D" NAS-IP-Address = 127.0.1.1 NAS-Port = 1812 # Executing section authorize from file /etc/freeradius/sites-enabled/default +- entering group authorize {...} ++[preprocess] returns ok ++[chap] returns noop ++[mschap] returns noop ++[digest] returns noop [suffix] No '@' in User-Name = "wyse1", looking up realm NULL [suffix] No such realm "NULL" ++[suffix] returns noop [eap] No EAP-Message, not doing EAP ++[eap] returns noop ++[files] returns noop ++[expiration] returns noop ++[logintime] returns noop [ntlm_auth] expand: --username=%{mschap:User-Name} -> --username=wyse1 [ntlm_auth] expand: --password=%{User-Password} -> --password=K503D Exec-Program output: NT_STATUS_OK: Success (0x0) Exec-Program-Wait: plaintext: NT_STATUS_OK: Success (0x0) Exec-Program: returned: 0 ++[ntlm_auth] returns ok [pap] WARNING! No "known good" password found for the user. Authentication may fail because of this. ++[pap] returns noop ERROR: No authenticate method (Auth-Type) found for the request: Rejecting the user Failed to authenticate the user. Login incorrect: [wyse1/K503D] (from client localhost port 1812) Using Post-Auth-Type Reject # Executing group from file /etc/freeradius/sites-enabled/default +- entering group REJECT {...} [attr_filter.access_reject] expand: %{User-Name} -> wyse1 attr_filter: Matched entry DEFAULT at line 11 ++[attr_filter.access_reject] returns updated Delaying reject of request 7 for 1 seconds Going to the next request Waking up in 0.9 seconds. Sending delayed reject for request 7 Sending Access-Reject of id 114 to 127.0.0.1 port 35826 Waking up in 4.9 seconds. Cleaning up request 7 ID 114 with timestamp +843 Ready to process requests.