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Classed as Spam by Large-Scale Free Email Servers?
bartle asks: "I run my own personal domain that serves all of my email needs of myself and a few friends. In general this has worked out pretty well but there's a fairly significant limitation: if I send an email to a Hotmail or Yahoo account that I've never contacted before it tends to get filed as spam. This means that if I'm writing someone out of the blue I need to send an email from a free service which kind of defeats the purpose of running ones own email server. My domain has a SPF record, the IP resolves, and it doesn't appear to be on any blacklists. I can not find any documentation on what hoops I need to jump through before Hotmail and Yahoo will consider my mail legitimate. I understand that there's a general paranoia about publishing information that could assist spammers but this attitude seems to be leaving do-it-yourselfers out in the cold. Does anybody have any ideas? Are there guidelines or protocols I can follow to make my email non-spam?"
Most likely your IP is listed at those sites as belonging to a range given out to ISP's for reistribution to their customers. You are probably rejected for that reason, because 'normal' domestic users don't have mail servers, or so these parties seem to wrongfully think. You can configure your mail server to send out the mail through our ISP's smtp server (smarthost).
Is it a static IP address that is from a "consumer" provider, i.e. did you pay extra for a static comcast address?
I believe that in those cases the reverse lookup of the IP address would either not resolve or would resovle to a generic name on your ISPs block, as opposed to resolving to your mail servers actual hostname (the host name identified in the messages headers. My understanding is that this is typically done as part of the HELO check).
In my experience having an IP address reverse resolve is one of the most critical components, especially when dealing with AOL. I have not had as much trouble with yahoo/hotmail.
-MS2k
Perhaps you have looked through your message for spaminsh words, perhaps not.
When I was tuning spamassassin on a daily basis, I got lots of surpizes related to what triggered the filters at first.
Many people put little ads in their sigs for example
We had a person who put their address in the sig. the problem was that they lived on 888 48th street (or similar address.) this looked like an 800 number to spamassassin.
If you really want to see a dumb message, have someone send you a cell phone picture mail. The did not get through our filters at all. When I white listed it, it had so much advertising for the company it addition to the bit map it was shocking.
Please post a copy of your standard email so we can see it. (#### out the to address of course)
Good luck