22 Mar
2017
22 Mar
'17
1:20 p.m.
This is not easy research, since the error messages you receive no one else seems to see. My problem may be that apple devices are no longer accepting self signed certs, but I have also looked at os x upgrades [home brew/openssl problems] for openssl.
If the OS is rejecting the cert (or visa versa), you'll see something like: Error: TLS Alert fatal: blah blah blah The original poster was getting all the way through MS-CHAP inner authentication, so it was could not have been a certificate issue since the TLS tunnel had successfully established.