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Ever since my first Mac computer (2008 - long before using FastMail) I've had problems with Mac Mail. After every major Mac system update I would try to configure it, have problems, then end up reverting to using my email provider's web interface. Just about every time it was related to SMTP settings.
Now IMAP/SMTP settings are pretty straightforward once you know what they should be (Fastmail included, old or new ones). If you enter them carefully they should work without issues or the need to troubleshoot them.
I prefer a Mac client so I tried a few and settled on AirMail, a ($10, App Store). It's straightforward to configure and has worked perfectly for me for over a year now.
As an aside, I spent several hours around Christmas trying to get my son's Mac Mail SMTP settings to work. I ended up having to delete the account and recreate it, which finally worked, but is simply unacceptable for a modern, mainstream application.
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