I have an single Exchange 2003 Server in a single domain. There are 2 iMacs on the network, but because of our naming convention of .local they can not be added to AD. So I allow their IP addresses to relay through the Default SMTP Virtual Server. It was working fine and dandy until today. For no reason at all it stopped working. Then I at least got it working internally, but they are unable to send outside of our exchange organization. I did a search and couldn't really find anything past DNS, but it's not an incoming issue. I hope somebody as some idea. Thank you.

A couple of things. First you can AD integrate your Macs into your AD even if you are using the .local DNS suffix. You just need to follow the instructions here: http://images.apple.com/itpro/pdf/AD_Best_Practices_2.0.pdf Secondly, even if you don't AD integrate them, you should still be aboue to run Entourage and have the clients authenticate to their mailboxes with the good old standard Domain\Username. This would alleviate their need to use SMTP relay altogether. Lasty, you have not provided any information as your issue other than it simply stopped working. What stopped working? Do the messages sit in the SMTP outbound queue of your Exchange server? Do the messages get rejected by the Exchange server to the clients? Do the messages get accepted by the Exchange server, but just dissapear? Either way, I would suggest using the Entourage client and stop using SMTP relay.