Exchange delays and then doesn't send email

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I would really like some help with this problem. We have Exchange 2003 loaded on two servers, one is for AV & spam filtering. The problem we have been experiencing is that mail sent to distribution lists is delivered to addresses within the domain, but not outside the domain. The sender receives one email message from “System Administrator” stating that “Could not deliver the message in the time limit specified.” After the timeout period, the sender receives another message stating “Could not deliver the message in the time limit specified.”, error 4.4.7. We’ve been through the authentication and DNS processes and everything seems fine. But the mail sits on the AV Exchange box under Server, Queues. I can force a connection, but the mail still isn’t delivered. I would appreciate any suggestions on how to solve this issue!

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Do the logs on the second server show that it is at least attempting to send to the correct addresses?

If you copy the addresses on the distribution list to the BCC field, do the messages go out?

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Are you sure the AV box hosts the external SMTP connector? Maybe it is specified as the expansion server for the distribution list but does not have a valid SMTP connector?

cheers, Paul

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Thanks for the replies. The problem turned out to be our spam filter on the AV server. We had turned on packet inspection to narrow down a Trojan infection and forgot to turn it off. This was flagging some distribution lists and closing the SMTP connection.

Again, thanks for the help!

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