POSTGREY or POLICYD-WEIGHT

[ephigenie]

I think - running with policyd and postgrey should work in almost 99% .
Sometimes it needs some time to have wanted mail receivers "withelisted" in policyd so after the first 4 weeks of operation it should look a lot better.

Hotmail & co are special cases you don't ever now how to make it right.
I've struggled badly with web.de i.e. (a big german freemail site) where all my mails got thrown into users spam folder right away.
In this case after contacting their support they put me ( better my mailserver ) on an automatic whitelist.
( this was for a relatively big partypics site i administer )

So before although we made everything right (our headers looked fine, we sent no spam and so on -> of course our mailserver allowed "call-back" and had a valid reverse entry ) we were on that "bad guys list" .
This happens all the time - sometimes accidently sometimes not.
Conclusion : It can be that you're doing everything right - and you're suddenly on a blacklist anyhow.