5 ms·
Tell HN: Expect you may have to write off Microsoft if you self host email
I've had this IP for almost a decade. It's not on spamhaus, DKIM and SPF are correct, and I've signed up for MS's Junk Mail Reporting Program and Smart Network Delivery Services. They still reject my mail with
> Unfortunately, messages from [45.55.34.226] weren't sent. Please contact your Internet service provider since part of their network is on our block list (S3140). You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors.
I went through their support channels and they were completely useless.
> Thanks for your patience while we investigated your request.
> Below your IP address(es) and their status(es) are listed.
> Not qualified for mitigation
> 45.55.34.226;
> The IP(s) above do not qualify for mitigation.
> Please note: This outcome indicates behavior that misses standards; please review Improving E-mail Deliverability into Windows Live white paper for helpful tips.
...
> What standards are missing? DKIM and SPF are passing and I got the IP taken off of Spamhaus recently. Other email servers like gmail aren’t finding an issue.
...
> Your IP (45.55.34.226) was blocked by Outlook.com because Hotmail customers have reported email from this IP as unwanted. One possible explanation for this is the automatic forwarding of unfiltered inbound messages, including unwanted messages, to Outlook.com/MSN addresses.
> Please confirm that your emails comply with Hotmail’s technical standards.
> For more detailed information about best sending practices to Outlook.com users, please review Outlook.com Enhanced Deliverability white paper.
...
> I’ve ensured there is no open relay, and I’ve only tried to send messages to my own Hotmail address so far. There are no other user accounts on this email server, just me.
> I’ve also signed up for the Junk Mail Reporting Program/Smart Network Data Services with that domain/IP. I don’t see any incidents there.
> Around what day/time was email reported as wanted?
...
> Thank you for contacting the Outlook.com Deliverability Support Team.
> As previously stated, your IP (45.55.34.226) do not qualify for mitigation at this time. I do apologize, but I am unable to provide any details about this situation since we do not have the liberty to discuss the nature of the block.
> At this point, I would suggest that you review and comply with Outlook.com’s technical standards.
> We regret that we are unable to provide any additional information or assistance at this time.
I've gone through all the links they sent me and nothing is wrong with my email server. It's impossible that I could have ever sent spam. They just decided they don't like me for no reason and I don't get to send them mail.
- gtirloni 4y ago> I do apologize, but I am unable to provide any details about this situation since we do not have the liberty to discuss the nature of the block This is what I find infuriating about Microsoft/Google. It's like a judge not saying what you're being charged for, just that you're going to jail.
- gus_massa 4y agoIn the university, we had some luck telling the students to send us a message from their hotmail/live/outlook/whatever address. This adds our address to some special secret list for that account, and our messages (usually) reach them. (It may fail. It may fail. IWOMM. YMMV. Sorry, but this is not a foolproof solution, just a hack. Sending email to new people is still difficult/impossible.)
- codegeek 4y agoThey are notorious for this and you are not the only. Not that others are far better but MS absolutely is the worst at this. Don't even get me started on their "Windows defender" flagging websites as dangerous.
- KomoD 4y agoYeah, Microsoft is always a pain in the ass when you're self-hosting email, that's why I just don't bother.
- jonathantf2 4y agoIt's because the IP is on DigitalOcean - a hotbed for spam and malware. I wouldn't bother self hosting e-mail any more because you'll come across most providers just not accepting your messages. Sucks, but is what it is.
- kevincox 4y agoFWIW I send email from DigitalOcean. And you are mostly right. If you are lucky you will get rejections. Most will just accept and put in spam which is better because the receiver can correct it, but worse because they will probably never see it and you won't know. Some inbox providers like Google, FastMail, Proton Mail and others will track your domain reputation if you are sending enough (~1 message per day seems fine) and once you have built domain reputation they will accept from DigitalOcean with no issue. But you can't rely on sending messages to new inbox providers. They reasonably treat mail from DigitalOcean IPs as suspect until they have enough other evidence.