Exchange delivery issues with free Internet e-mail accounts

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Free e-mail providers like Hotmail and Gmail have proliferated with the growth of the Web as a whole. Administrators sometimes encounter problems when sending mail to such providers from Exchange servers. Many of these issues stem from minor Exchange misconfigurations. Here's some advice to help you troubleshoot these types of problems.

About the author: Serdar Yegulalp is editor of the Windows 2000 Power Users Newsletter and a regular contributor to SearchExchange.com.

I'm concerned about the portion regarding EDNS and the section on PIX firewalls and EDNS. The answer here is NOT to disable EDNS, but rather to update the firewall to support the longer UDP packets.

Who's to say that a hotfix, service pack, upgrade or additional service installation will not restore or require EDNS? We've all made changes to get something working that we don't remember later, and then we waste hours chasing down the problem.

Addressing the issue with PIX firewalls (or others) is the best course here, not crippling the EDNS service. Fix the problem, don't stick a band-aid on it.
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b>—Gary K.

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Thanks for the comment -- yes, my statement was meant to imply that it is always best to upgrade/patch the firewall if that option is available, with disabling EDNS as a workaround if that isn't possible or doesn't have the desired effect.
—Serdar Yegulalp, tip author

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Good article except it does not explain what the reverse DNS settings should be. Should the IP address point to FQDN of the e-mail server? What if you have more then one e-mail server? Should the reverse DNS just point back to the domain name?

I had an issue which I think I resolved but was unclear on what the reverse DNS should be. Right now, I have it pointing to the FQDN of my e-mail server.
—Doug S.

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Creating reverse DNS records isn't difficult. When configuring DNS for a mail server, set up a PTR record in the in-addr.arpa domain for each MX record (as described in RFC 1912, section 2.1). If you're dealing with a multi-homed host or with multiple email servers, each IP address must have a separate PTR record as well. The IP address for the e-mail server should point back to the server's FQDN -- i.e., mail.thisdomain.net.
—Serdar Yegulalp, tip author