DNS issues using exchange active sync over WAN

  • I currently use a pfSense in a production environment with 1 wan adapter. The WAN adapter is actually a point to point leased line which doesn't carry any internet traffic so the assigned IP is an internal one in the range of

    The pfsense box does the dhcp and forwards the dns to an active directory server at the site over the WAN link.

    The problem i am having is that outlook will periodically prompt for user credentials, as if the connection has been lost, this happens on all workstations that are connected through the pfsense box, if I plug into a WAN router, it behaves normally so pfsense appears to be blocking something somewhere but even after looking at the firewall logs i have drawn a blank.

    Could anyone help me resolve this issue?

Log in to reply