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Silly question, but have you tried sending an email to someone running spam-assassin and check the headers of the received mail to see if there's anything obvious flagging you? For example, on Linode make sure that your reverse DNS for IPv6 are also set correctly.

I find it hard to believe that you get classified as spam for no good reason, unless perhaps that Linode / Digital Ocean are known for hosting so much garbage and people can be tempted to outright block them, but I doubt Gmail does that?

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