I have a new Entourage 2008 client to add to my Exchange server. I connected as required with DAV and the client can sync and receive mail. But all outgoing mail that the client sends it tagged by the receiving server as spam. Here is the reason that they report: RCVD_NUMERIC_HELO Received: contains an IP address used for HELO Have I setup DAV incorrectly on my server. This doesn't happen when I use Outlook, OWA, iPhone, or other handhelds. Only with the new Entourage client. I can attach the entire header to the message if needed. It shows the server names and IP's. Thanks

Hello,This is some kind of bug i guess... check out this Rules/RCVD NUMERIC HELO SpamAssassin Rule: RCVD_NUMERIC_HELO Standard description: Received: contains an IP address used for HELO Explanation In an SMTP session the argument to the first command a client sends (EHLO or HELO) should be the client identifier. RFC2821 specifies the fully-qualified domain name of the SMTP client, the older standard RFC821 refers to the host name. In situations that the client does not have a meaningful domain name the client SHOULD send an address literal (an IP address enclosed by square brackets). If a Received: header is parsed that indicates the EHLO/HELO identifier was given as an IP address, but not enclosed by square brackets, this is in violation of the RFC. Arun Kumar | MCSE - 2K3 + Messaging | ITIL-F V3

Any update on this?Arun Kumar | MCSE - 2K3 + Messaging | ITIL-F V3

No luck yet. I only see problems when sending to certain mail servers, specifically ones running spamassassin with that certain check enabled. I do understand the problem, that the HELO response is a number IP, instead of a FQDN. But I'm not sure how to fix this. The Exchange server has been in production for many years. And it runs several local Outlook clients, remote HTTP over RPC clients, OWA clients, and POP3 clients all without any issues. (they don't get the Numeric IP error when sending mail) So I'm guessing my problem is in the OWA or HTTP-DAV setup on the server. But from what I can find Entourage just uses OWA. But I don't have the problem when using OWA. It only happens from my single entourage client. When I setup the Entourage client I didn't have to adjust anything on the Exchange server. So right now I'm not sure exactly where to look. Thanks for any suggestions,