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by darklajid 4231 days ago
Funny enough my own server ONLY had problems with .. GMail so far.

From two days ago: "Let's try this GPG setup, write a mail to my coworker's private GMail account and get a verification that everything checks out on his side".

GMail refuses the PGP/MIME mail, bounces after end of DATA, as 'Spam'. What?

Send the same mail to my GMail account. Works.

Send the same mail to my brother's GMail account. Works.

Send to coworker again: Bounces after DATA, refers to a useless website that offers Google's policies for bulk mails again.

Send a plain text mail to coworker, complaining about Google's mess: Accepted.

So.. Takeaway:

- Google randomly rejects mails from my server, without anything I can do and without providing any information WHY it would do that. Not filing as spam, rejecting outright.

- Google only did that with a mail that is unreadable (PGP/MIME). Coincidence? Make of that what you will..

I will keep my server though. And loudly complain to people that run broken setups. In this case I complained to this coworker of mine and wrote lots of expletives directed at Google - and the issue is resolved for me now. People with GMail addresses that don't get my mail are frankly not my problem and for friends and family I might be able to exert enough pressure to fix the problem.