Miserable, this kind of stuff is why I don't run my own mail server any more. Happy Fastmail customer since 2006.
It's really hard to run you own mail server. Much harder than a web server. This is bad for freedom on the internet. http://www.ebb.org/bkuhn/blog/2015/09/15/email.html
Gmail marks my mail as spam, for new recipients, though. I don't care, every gmail user usually checks his spam anyway and when I do care, I'll call person to ensure he got my mail, regardless whether I use gmail or my server.