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> Said that it was because my mailserver did not send enough legitimate mail for their algorithm to trust it.

In other words, a small self-hosted email server will be considered a spammer until it starts sending out large amounts of email? Maybe that can be automated...

In theory it would be simple to provide a "cloudworkers cooperative" kind of service that just bundles the outbound mail so that traffic is sufficiently large to be whitelisted by the big providers. The two biggest problems are A. Scaling up sufficiently without attracting Spammers. Because even a single Spammer can ruin your reputation forever. So ideally you'd have a tight knit group of friends or similar. Even then you could hardly assure than no one ever gets hacked. B. Edge Cases. Even if your US or West European Traffic is sufficient to be whitelisted by all major Providers, how do you ensure that the occasional Email to a customer of an Indonesian ISP does not get blocked by their provider...

Yeah SMTP relaying is quite common. The problem is due to email architecture, to my knowledge, that same relay is going to be able to read your incoming emails because remote servers will block emails from user@endserver.org sent from relay.net unless endserver.org has MX entries pointing to relay.net.

That is less the case today. Back before SPF, absolutely. Today, with properly configured SPF records, not so much.

'large amounts' is also pretty relative, I'm sure if you had a small team of 10-25 employees on a self-hosted mail server (preferably with a static IP via the ISP) you'd be taken seriously pretty quickly versus only you sending an email once a week or less.

I'm sorry this happened to you, but it's a shame. You end up giving money to your perpetrators and leaving the rest of us in the same situation you were in previously.

Maybe a hosting coop could be an option? Large enough for reputation but ethical enough to still federate with smaller hosts?

Agreed. But I did learn a lot from it. I needed that because in our large organisation at work the admin rights are highly compartmentalized. And this way I was able to understand what other admins were and weren't able to do.

You can actually get a free test tenant from MS for 3 months but setting up a real production environment is much better than doing some tests.

But yeah I feel lousy about it.

I tried office 365 for email this year but couldn’t get the marketing emails from Microsoft under control. No matter how much time I spent trawling through the settings menus. Almost every email I got was about some security update or promotion from some ms product I did not use and had no intention of using. And I was paying for O365 too!

It is possible. I managed to stop them in the end. One of the many admin sites if I recall correctly (seriously, they have an office admin portal, exchange online admin, Azure Ad portal and everything is spread out across those)

If you use hotmail.com a lot of legitimate email goes to spam. I see it as a problem of the hotmail users, not mine as a sender.

I host my own email and I have the same problem with MS. Perhaps this is something for the new Digital Markets Act and interoperability laws in the EU to handle.

You can configure postfix to relay emails to certain domains through a 3rd party SMTP service like SES. The MS domains give all of us the same problems, there is no other solution.

Thanks I wasn't aware of this option. I'll consider it. Thanks for the tip! At least I'm not the only one but I'm sorry you're experiencing this too.

You may just have been unlucky with your IP block having spammers. How were you hosting it - own ISP or another provider?

I have not had deliverability issues for years with my Kimsufi (OVH France) server. While I am confident my server is well configured using best practices, I suspect some of it is also just luck not to be in the same IP block as a spammer.

I was using a colocation hoster in Belgium. They actually moved me to another netblock to test (they were a really nice small company). But the same happened.

I heard Kimsufi is indeed pretty bad as it's so cheap people tend to use it for 'throwaway' purposes. It's basically the white label budget brand of OVH :)

I've had 2 kimsufi email servers and both were fine. It shares the same data centres as OVH so I guess IP ranges are similar. No problems with blacklisting based on anything other than my own misconfiguration so far, and it's been maybe 8 years.

I had a very similar experience. Is there any cheaper option than just using aws SES nowadays ? (for outbound only! don't understand why people would pay the same rate for inbound) My concern is what happens when aws decides to massively increase rates...

If you send from an ec2 instance is "always free" (tm) for the first 62k outbound emails each month and 1k inbound.

> This way the big players can just carve out a bigger market for themselves.

Or it’s because there is a near infinite number of domains so it’s relatively simple for spammers to avoid bad rep blocks by grabbing new domains and starting fresh.

Yeah but then why keep putting me on the Blacklist every month? After I've been in touch so many times.

Moved away from outlook.com hosting a while ago since so much legitimate transactional email went to spam whilst actual spam easily got through. Now, when outlook forwards to gmail, gmail catch it before it hits the inbox.

Corporate O365 users often have their own Exchange server (cloud or self-hosted) with custom configuration.