@jaredbusch Yea, I can't think of anything else that would cause it either... I haven't upgraded any of the systems that i used LE on to 14 yet to try them.
I found a GoDaddy cert at a client that had a SAN that we were no longer using right now. SO I updated that DNS to point to my test PBX instance and loaded that cert onto my PBX. I changed the active certificate in SysAdmin and told the phone to provision to the new DNS name and it immediately provisioned.
So the problem is definitely the LE cert or cert process.
We at least know where the issue is now.