I'm going to have to try and do that, unfortunately the person who set it up is no longer with the company and we just have an outsourced IT company that maintains it and they usually aren't very help fully. However, because the web tools were able to connect to is it reasonable to assume the problem is on my end? I was thinking maybe because I dont have a domain name so if the Exchange server tries to lookup the IP address of my computer there is no MX or PTR record. Is this something SMTP servers look for?
I also found something that I dont know how to explain or how it may affect this. The MX record for the server list exchange.mycompany.com. However, even when I'm on VPN, I can't connect to the SMTP server using that address in telnet or the IP address it points to. I have to use remote.mycompany.com, which is shown in the SMTP banner and points to the SAME IP ADDRESS. Is there a setting in Exchange that makes it script only request coming from this address? If so, how do the online SMTP tools discover this subdomain when I only gave the tools the domain name (mycompany.com) and the MX record only shows exchange.mycompany.com? The address remote.mycomany.com is not located anywhere in the zone file.