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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?"
Rather than connecting directly to Yahoo's or Hotmail gateways, use your ISP's mail relay. That's what it's there for.
http://www.justfuckinggoogleit.com/