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Comment by jbergstroem | Hacker News Reader

I'm also one of those oldfarts that insists on hosting my private emails for me and a few friends. I've owned the ip since early 2000's and have had zero "spam"/blacklist incidents. One trend I've been noticing is that Microsoft/Outlook have regularly started to block me. I have to contact their abuse which takes a day or so to get unblocked. To date, I've done so >10 times:

   hotmail-com.olc.protection.outlook.com[104.47.1.33] said: 550 5.7.1
   Unfortunately, messages from [<redacted>] weren't sent. Please contact
   your Internet service provider since part of their network is on our block
   list (S3150). You can also refer your provider to
   http://mail.live.com/mail/troubleshooting.aspx#errors.
   [VE1EUR01FT028.eop-EUR01.prod.protection.outlook.com] (in reply to MAIL
   FROM command)
   Reporting-MTA: dns; <redacted>
   X-Postfix-Queue-ID: 14A41FEB66
   X-Postfix-Sender: rfc822; <redacted>
   Arrival-Date: Thu,  14 Mar 2019 14:07:42 +0200 (CEST)

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I host my own email stuff too (private stuff and for a couple of friends) and sending to microsoft domains (hotmail, outlook.com) consistently gives me the most problems. Right now it seems to be ok again but I always make sure that people using my domains are fully aware of all these problems.

Edit: not long ago I used a gmail account to contact microsoft support to get them to remove me from their blacklist again (couldn't use my normal email for obvious reasons). Ironically enough their reply got marked as spam by gmail (something in my included message parts might very well have triggered that but I had to laugh out loud at the situation).

I'm trying out purelymail (basically one dude's AWS hosting of email for $10/yr) and I'm having the same problem with my custom domain: google stopped having issues after the first few emails I sent got marked as "not spam", but microsoft, despite the purelymail guy filling out all the requisite forms, still eats all of my email, not even sending it to the spam folder of the addresses I'm sending to.

Don't worry, you can fix all of this by joining the ReturnPath Protection Racket™^W^W "Sender Certification Program" that will let you pay to guarantee your mail ends up in the Inbox at all the major players.

Ever tried https://protonmail.com/ ? I wonder if they face the same kind of challenged?

I've never gotten spam nor have my ProtonMail emails marked as spam. Lucky me

At >10 times I'd automate that process.

Hrm, an automated appeal to automated spam-listing probably looks a lot like spam to the algorithms used to detect spammers.

Form has captcha: https://support.microsoft.com/en-us/supportrequestform/8ad56...

Is it illegal to pay for one of the captcha solvers? Ones like this are the easiest, captcha solves cost something like 4 cents each, and all you do is send the image to an API, which responds with the solved captcha.

Captcha solving services are cheap

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