I have two Asterisk's connected via IAX, they are sitting on the same
network, via a VPN, so there should be no problems with firewalls.

Huh? How can they be on the same network "via a vpn". If there is a vpn, then they are on two different networks, but "connected via a vpn", which would imply that there is a firewall/router of some sort that could be blocking traffic.
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