Following is an additional post for the thread I started this morning, thank you.. Thank you for you help with my previous post. I have some additional questions also: Question #1. As for the RADIUS requests not getting to the server, I have a question about the value of "ipaddr" in the "clients.conf" file. All of the instructions that I have seen have been unclear about what this value this should be set to specifically.. Should it be the IP address of the computer hosting the Radius server (192.168.1.113), or the IP address of the router (192.168.1.1), or some other value? I have tried all values and still get the same error message. Note that I have not yet set the ip address of the server computer to be static in the "/etc/network/interfaces" file. Following are the questions about this: Question 1a: What is the best value to use for the "ipaddr" variable in "clients.conf"? Such as the ip address of the server computer, ect.. Question 1b: What is the best value to use for the "Radius Auth Server Address" setting in the router (using DD-WRT)? Presumably it is the same value as 1a? Question 1c: How important is setting the IP address of the server computer to be static while testing even though I am sure that the IP address of the server computer is currently 192.168.1.113 for the time being? Question 1d: What is the best source of information about this issue if the answer is complex? _____ Question #2. Version 2.1.12 of FreeRADIUS is the one that was installed when I entered the "apt-get update" and "apt-get install freeradius" commands. What would be the biggest benefits of upgrading to a newer version? Presumably I would need to reconfigure from scratch if I upgraded, am I correct? I have a feeling my problems are elsewhere for the time being if the user client computer is not connecting to the server though. _____ Question #3. When you say "Users cannot manually configure their 802.1x settings" on Mac computers starting with OS X Lion, do you mean that it is mandatory to configure Mavericks using the XML method? I'm currently trying to configure the networking manually in the "Network > Wi-Fi" section of the prefs by selecting "WPA2-Enterprise", then "EAP-TLS," and it does seem to be taking all of the necessary information and it even gives the name of the certificate as a pull-down option, however it then says "invalid password" when I try to connect. ____ Question #4. As for the certificates, they are being created using the "sha1" method like you suggested (typed like that rather than "sha-1" if that makes any difference.) The "default_bits" are set to 2048. Following is the command I used to create the DH file: "openssl dhparam -check -text -5 1024 -out dh". I have seen some instructions that say to trim sections out of the certificates using a text editor before using them with a Mac, would it be helpful to do that at all? Thanks for your help!