Howdy, We have a single Exchange 2003 server that is offsite at a remote location with one of our AD servers.We have a PTP VPN between our office and the exchange server that is wide open.The exchange server has an external ip and an internal IP..if I am external to our network and use the FQDN for the exchange server I can send SMTP with the SSL required box checked. If I use the external IP address of the server while external it works fine and sends mail also.But when I am in our office or vpn'd into the network the FQDN (which while in the office points to the internal IP address) or the internal ip address directly fails to connect.Our outlook clients conencted to "exchange" are fine and so are our Entourage clients. It's just a few MAC's using Imap and SMTP w/SSL that fail to send.Internally the name resolves to the right IP, nslookup resolves correctly and I can telnet to port 25 to the FQDN and the Internal IP while in the office. Any Ideas? Any thing to tests?(I am aware that this might be an issue with the VPN but the good folks on the MS forums are more responsive with suggestions)Big thanks..Moe

Hi, Please check whether I understand the problem correctly: 1. The internal POP3/IMAP4 account (MAC) is unable to connect to Exchange Server to send email (through VPN or in the Office directly) 2. You are able to telnet to port 25 to Exchange server in the internal network (VPN or in the Office directly) by using FQDN or internal IP Address. If I am right, I suggest you use Outlook/Outlook Express to configure a POP3/IMAP4 account to check whether the issue still persists. Mike

Yes,People using Mac Mail (IMAP/SMTP) can not send mail while in the office or connected to the office via VPN while using the FQDN or internal IP address for the server.Outlook users can.