Thank you for the breakdown of what each of those do. That definitely helps me understand the process and what's going on. At the end of the day using IPsec is a great idea. We have talked about using that with other systems in the past. That is definitely worth bringing up as an option at work. The other option that is appealing is TTLS/PAP. I spun up a server at the end of the day today to start testing that out. Does it play well with active directory using Kerberos? That option sounds nice because traffic is encrypted at both ends of the FreeRADIUS server. I had been doing some research to get a better understanding on how all this worked. Alan DeKok had some great references at deployingradius.com to help me understand how all this works. I really appreciate all your guys help and feedback. I wasn't sure if FreeRADIUS had an active community or not. I've not seen a lot of talk in the freenode IRC channel. Its really nice you guys have something like this mailing list setup.