Hi Steve! Sorry to hear you're having trouble with this! Based on your description above, it sounds like these two domain names might be setup on separate sites in IIS, is that correct? In that case the two sites are likely fighting over port 80 and so that's why you're finding only one will work at a time. To resolve that I recommend moving all of the SmarterMail-specific hostnames to a single site so that all of those bindings answer on the same site. This will allow IIS to decide whether port 80 is allowed or not based on the hostname users are requesting, and should prevent any conflict between the two. If you have separate public IP addresses available for those hostnames you can also configure those bindings to use that specific IP while you're in there. I hope that helps!
Kyle Kerst
IT Coordinator
SmarterTools Inc.
www.smartertools.com