I run a couple of mail servers and the beginnings are always a bit rough, but then everything works (mostly) fine. I start by asking Microsoft to unban my IP (for some reasons the IP range with my favorite hosting provider are banned by default by MS servers). They lift the ban and since I'm a good netizen and use my servers strictly for the communication with the customers (and never for marketing), I never have any problems with delivering to outlook.com, hotmail.com, etc.
Google is a different beast. Last time I remember I had to do strange things like disabling IPv6 support in my MTA (which is a good idea anyway as I'm not an expert in IPv6) in addition to the usual SPF setup etc. E-mail is delivered in general, but once in a while some letters go into spam for unknown reason. But this happens rarely, maybe a couple a times a year.
Whenever I set up a new server, I have to start from scratch though.
Google is a different beast. Last time I remember I had to do strange things like disabling IPv6 support in my MTA (which is a good idea anyway as I'm not an expert in IPv6) in addition to the usual SPF setup etc. E-mail is delivered in general, but once in a while some letters go into spam for unknown reason. But this happens rarely, maybe a couple a times a year.
Whenever I set up a new server, I have to start from scratch though.