Port 80 is already open on your E-Smith machine, he simply opened TCP 80 on his side so he could communicate with the server (It seems). On a side note, WatchGuard is a worthless piece of Win32 garbage. It causes more problems and offers little or no security.
My recommendation: Use FTP, HTTP uploads are known to be slower than other alternatives. Are you guys using some type of POST to upload the data to an HTTPD server? Why not use FTP? Why not create your own Winsock application? Are you compressing the data before you are transferring it?
Hope this helped,
Nathan