At that time MS had a third party that managed this, you could pay them to do something that would basically get you whitelisted; but this was for an SME and the cost was prohibitive for the potential benefit.
If you moved server on AWS presumably you'd have to go the same route again - who did you contact? - would you be 100% confident you'd get whitelisted?
I wonder if the fact that you have done it for decades helps with you avoiding spam filters. This may not be the experience for someone who newly sets up their own email server.
I've set up mail servers many times over many decades and it's not as hard as a lot of people think. For a reasonably secured and maintained personal server, you'll have to learn about SPF, DMARC, and do more detailed DNS setup than you do to get a quick website up, but once up, everything should go well... so long as you and your family behave.
For businesses, especially those with enthusiastic marketing teams, it's harder because all it takes is a a bug in some transactional email code, or a bad email from a well meaning sales rep to some email list from a "digital marketing" forum to completely wreck your server's reputation.
Working as intended if you ask me.
http://go.microsoft.com/fwlink/?LinkID=614866
You can also join the "Smart Network Data Service" (SNDS) program, which can alert you in the future if you are re-listed and sometimes will provide additional information about why the IP has been listed.
Microsoft only provides delivery mitigation for large-volume senders. Small-volume senders (i.e. not spam senders) will not be provided delivery mitigation. That's from my personal experience anyway.
> You can also join the "Smart Network Data Service" (SNDS) program, which can alert you in the future if you are re-listed and sometimes will provide additional information about why the IP has been listed.
Unless you are a large-volume sender, you will not be able to get ANY information out of SNDS.
Currently I am running Postfix on my FreeBSD server, and not using SpamAssasin. I've had this setup for years and it's less than ideal but it's at the point where it's been hard to justify the time I'd have to spend setting up a better configuration.
I ssh into the server and read mail using mutt. I also have notmuch installed but only use it a little bit now and then and still relying primarily on mutt. I'm not really happy about mutt either. It's neat in its own way but it's also a bit of a drag to use and even though I enjoy using the command line I don't feel like mutt is really a good fit for how I would like to use mail.
Ideally I think I'd want something similar to how some of the features of GMail work, but mainly in terms of tagging and filtering. As for a web based interface, I don't want that part really. But still very much interested in knowing of web interfaces too from people that use them and like them.
But most of all, what I am looking for is a server that has good and easy to use filtering, that is open source and runs on FreeBSD or Linux, and native clients for macOS and iOS that integrate well with the server including the tagging and filtering stuff.
This is the sort of thing that puts me off self-hosting email, as much as I'd like to do it -- it seems like a huge amount of effort, tracking down who I need to shout at this week to have them whitelist my IP address.