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> Gmail is relatively easy to appease, mostly just configuring your nameservers and email headers to Google's standards,...

Do you mean SPF, DKIM and DMARC or something else? I will check the records again, just in case, but afaik they are perfect and Gmail still often classifies my mail as spam. It is annoying as hell (and your comparison to playground bullies is very apt).

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SPF, DKIM and DMARC, but there's other factors as well. Gmail will usually tell you exactly why something was flagged spam. If you go to "Show Original" SPF, DKIM and DMARC should all show "PASS" if everything is configured correctly.

Interesting, didn't know that as I don't use gmail myself. Thank you!

Hmm, not always. I've just setup my own mail server, I PASS SPF, DMARC and DKIM according to Gmail headers and yet my email is still classified as spam, as determined by "Gmail magic". I believe this is because the domain is relatively new and Gmail treats you as guilty until you prove your innocence (ie. Enough people mark my emails as not spam)

Try adding an IPv6 address. Got the tip here on HN.

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