The issue is, I've done everything, a semi-competent Linux user with Critical thinking skills should do, I've been methodical. asnd disciplined and persistent. Yet still, I cannot succeed at this. This will make my University Career look bad. I just think I could use another pair of eyes, maybe I missed something.
I feel like Edward Elric searching for the Philosopher's stone.
I posted an idea and you decided not to reply to my questions ! I suspect that your VPN server doesn't know Microsoft Radius attributes and refuses to send them to the radius server. I've tested a bad setup (lack of Microsoft radius dictionary), and I get the same radiusd -X debug log: no MS-CHAP Challenge in the request... I asked "have you checked possible error messages in /var/log/messages " on the vpn server ? To be more specific, look for the following lines in you log file: " rc_avpair_new: unknown attribute" If you see such lines it might be that your radiusclient library (used by the PPPd plugin on your VPN server) doesn't understand the Microsoft attributes (for instance the MS-CHAP Challenge). Thus, the PPPd radius plugin doesn't send these attributes that are required for Freeradius to do MS-CHAP authentication. Could you really check that your dictionnary file on the VPN server side contains a line like: INCLUDE /usr/share/radiusclient-ng/dictionary.microsoft and check the content of this file... HTH, Thibault