The question is, how do I get out of having my own email labeled as spam by the big providers?
Are you sending from a "consumer" network IP block (cable modem or DSL)? If so, that's going to be big points off (probably not since you are sending through fastmail).
In my limited and somewhat dated experience, some email service providers are very aggressive in blocking email senders. The better class of these had contact information and would respond to requests to be whitelisted. Some email providers blocked emails and had no contact information to request white-listing. For them, my only recourse was to send emails to them through an email forwarding service (I used Dyn at the time, Dyn apparently sold their email forwarding business to DuoCircle).
https://en.wikipedia.org/wiki/DMARC
Thanks a lot, always good to have a starting point.
My $.02 on the conversation is to double check your IP on some of the RBL services http://www.anti-abuse.org/multi-rbl-check/ to check to see if you are listed for any reason.
And then send a test email to https://www.mail-tester.com/ and check their scores. You SHOULD be able to get a 10/10 with a blank email as long as your authentication aligns.
Feel free to email me and I would be happy to help.
https://penguindreams.org/blog/how-google-and-microsoft-made...
I have DKIM, SPF, DMARC and reverse DNS all setup. I've moved to a provider that disallowed 25 in/out and you have to specifically request it be unblocked.
I still have this issue. There is no real way around it. Microsoft and Google's spam prevention algorithms are very over-aggressive and will push out anyone with a personal e-mail server.
Each time you send an e-mail to a new person you've never e-mailed before, contact them on Twitter/Facebook/Reddit/Discord/whatever and tell them you sent them an e-mail and to mark it "not spam." They'll be able to receive your e-mail from here on out (just don't include any links).