[MortenK]

OP, I don't know if you are reading the comments here but in case you do: Don't get discouraged so quickly.

The reason this is happening is as the blurb from the MS postmaster help page: Your IP doesn't have a reputation yet.

The reason these rules are in place aren't about email monopoly, it's about spam. If anybody could setup a SMTP server and start firing off large amounts of mail, spam would be even more endemic than today.

You can configure your server perfectly, but that doesn't mean much, since it's your IP that's the problem.

If you have legit objectives, it's a pain in the ass for sure. But you are not the only one having this problem, and there's a solution for it.

All the big email service providers (ESP's) like Neolane, Exact Target, Mailchimp, Campaign monitor etc share this problem when they onboard a new client, who requires their own IP.

Deliverability is a surprisingly deep, technical topic, and all major ESP's have entire teams of specialists working on this.

If you want to make such a service as Fastmail, you need to get really into deliverability. It's not a walk in the park, but it's not impossible either.

I'm not a specialist in this particular area myself, so I can't give you that much specific advice. I've just worked elbow to elbow with a lot of these guys, so I know what kind of challenges they work with.

One thing I know for sure is really important, is the "warming up" of IP's. Basically the IP you are sending from needs to accumulate some reputation over a period of time, typically a month or two.

If you send out reasonably small amounts of mail to email addresses that exists and the recipients does not explicitly report you for junk mail, your IP get whitelisted and you will get a much higher delivery rate.

There's no quick fix unfortunately, and email reputation is hard to gain and fast to lose.

But it certainly can be done. You sound very competent on the server side of things, so to get your fastmail-like service up, I think it's just a matter of a bit more persistence and studying deliverability as a technical subject.

Hope this helps.

[jodyribton]

Thanks for the encouragement! I might take another shot at it sometime. I had this server running for about 3 months with just my personal mail, sending probably 1 email per day on average. It's possible slightly higher volume would do a better job of "warming up" the IP.

I self-hosted from about 2007-2008 and 2011-2013, and had nowhere near as much trouble with deliverability. It came as a bit of a surprise how much more difficult it is these days.

[MortenK]

If you try again, try to see if you can get a client with a decent sized mailing list. Warming up is usually done with progressively larger sendouts. So you'd start with maybe 500 sendouts, then a thousand, then 3000 etc.

But anyway yeah the barrier to entry has risen really much. It's much harder these days than just a couple of years ago, and it probably won't get easier either!