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All emails I send from my new server go to spam in Gmail (and sometimes yahoo).

I've never before sent out mass email or spam.

What I've already done:

  1. Configured reverse DNS
  2. Enabled DKIM
  3. Verified my IP is not on spam lists
  4. Verified I'm not an open relay

Here are the headers from the received message: http://pastie.org/pastes/8450781/text?key=onxgrau1xinyqv7ridxrea

Really, can't seem to figure out why the mail just doesn't come through.

I'd really appreciate your help. Thank you!

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I had that kind of problem with Google Mail in the past. I had everything set up properly, just like you did and still had my mail going to GMail's spam folder. The best what you could do (what I did) is to keep marking the messages from your server is Not spam. Ask few of your friends to do the same.

In time, the issue should be resolved!

I recommend reading more from Google's Support:

Why messages are marked as Spam?

If you're confident that the message is not malicious, click the Not spam button to move the message out of Spam and into your Inbox.

To prevent these types of messages from being classified as spam in the future, you can do one of the following:

  • Adding their email addresses to your Contacts list. Gmail will deliver messages from members of your Contacts list to your inbox, unless we know with high confidence that they are spam.
  • Creating a filter so the messages are never sent to Spam.

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