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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).