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My experience is slightly dated (2 years), but I've always had the best luck running my own sendmail setup on a box I own/maintain.

SPAM flagging will have a lot to do with content, and some to do with your source IP (IME). Sharing a server (and source IP) with a bunch of other people doesn't help your odds.

Owning and controlling the server, the DNS records (forward AND reverse), plus sending a few test messages to test accounts, has always seemed to work best for me personally.




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