Thank you for the feedback. I opened a ticket with our provider as well and they just responded that the call was “failing on an invite response” which jives with your re-invite hunch. They suspect it is the extension CID responding with internal info and not the DID so I’m exploring that now.
I did see that I can post links now. I’ll use the pastebin in the future but the links I provided where wide open with no authentication needed (cause I hate that stuff too!)
As for the pfsense… I’m more than confident that it is configured properly as it is the same setup as most of my other clients have and they have no issues, even with the same provider.