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I am coming to the point of thinking this is beyond my ability to accomplish.

I have repeatedly built new servers on Digital Ocean (3 so far) with Postfix, Dovecot, DKIM, pretty much everything out there, and then in the big moment, send an email to myself at gmail (or my testing email on hotmail) - aannnd.. it's in the spam box.

NOTHING I've done has ever allowed me to get an email to Gmail from a server I've set up that wasn't marked spam and furthermore, even after reporting it as not spam, the next one still goes into spam.

Questions are:

  1. How can I get the details of why the email(s) were sent to spam, or the report?
  2. Will it help at all to continue sending emails to friends and people I know (like a family newsletter or something) and have them look for it an unmark from spam?

Thank you

  • I had to use ESMTP, set up reverse DNS all using the name the mailserver uses in the HELO, and list the server (well, all MX records for my domains) as my servers in a SPF record. IIRC gmail will ususally tell you why it got sent to the spam, you may need to read the headers to determine. Also check the various blacklists, etc. for your name and your IP. – ivanivan Sep 14 at 4:23
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    When you view the message in Gmail, there is a large box with the heading "Why is this in spam?" – Michael Hampton Sep 14 at 7:28
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You could refer to the followings: https://www.quora.com/Messages-I-send-with-gmail-are-marked-as-spam-Why

When you select your spam folder, click on any message and at the top of the message you'll see an explanation for why the message was marked with spam. https://lifehacker.com/gmail-now-tells-you-why-email-ends-up-in-your-spam-fold-5894793

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