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Introduction: I have run my own mail server for more than 10 years, and I never had any problem with Gmail, so far. But I needed to complain regularly (like every year) to Hotmail, because they were sending me directly to their Junk folder. So I used to fill in an online form they provided, and they removed me from their mysterious blacklist for a while (they didn't give reasons, they didn't even answer, actually).

But recently:
A few months ago, the nightmare really began!
I'm now going directly on SPAM/Junk folder both on Hotmail and Gmail, with all my domains.
The processes to get out of this are murky.

Microsoft way:
Microsoft changed his process, the form doesn't exist any more, and you now have to apply to a SDNS/JMRP program, which doesn't really help.
I've tried to use an Hotmail account to apply to this program and guess what?
Yes, mails from snds-authorization@outlook.com landed directly in the Junk folder.
How can they help me if they reject themselves?

Google way:
Similarly, Gmail is asking you to subscribe to Postmaster Tools, which doesn't help at all because it needs you to reach a certain volume of mail I'm far from, in order to be effective.
So it's easier to avoid being rejected if you are mass-sending???
I can only access those empty interfaces, and I feel like I'm in front of a big wall.

As many already reported elsewhere, declaring the mail as "non-spam" doesn't solve the issue and the next mail still end up in junk folder (for both Microsoft and Google). Plus this is not a solution anyway.

My situation:
I always have respected every standards (SPF / SenderID, DKIM, DMARC, reverse DNS / PTR).
I DON'T use this server for mailing in batch or marketing, this is my personal mailbox and I only send (very) few messages to my legit contacts (family, friends & customers). Those contacts always expect my mails, and recently they have to check the spam folder, just for NO REASON, even when I simply answer back to mails then sent to me.
I don't send message looking like spams, I don't attach quircky PDF or such things. I don't make use of my broken English since I use my mother tong in most of those e-mails.

I'm not blacklisted anywhere, I've checked many blacklists list on the web.
I'm not a backscatter.
I'm declared OK by SenderScore.
I get 10/10 at mail-tester.
I even subscribe, few years ago to dnswl.org.
Finally, I must add I'm NOT an open relay and my server have not been hacked.

Conclusion:
I'm desperate to understand why this struggle.
I mean I understand SPAM is a big deal, but after having accumulated knowledge for years (managing Postfix can be tricky) and applied to all standards, I feel like I'm punished for not being one of the giant out there.

Am I missing something obvious?
Or do Microsoft and Google just decided to kill personal mail servers?
Please help!

BEFORE ANSWERING THIS: I know some of you will quickly deal with that question by tagging it as duplicate. I already read about it on this very site:

All this questions ended-up unanswered or not fit with my case. So maybe we can try to do something different here and discuss about new ideas or other places where we can actually find an effective answer.

If the answer is contact them to ask why they rejected you then it fails greatly. Because as mentioned, there isn't anywhere to get such contact.
When dealing with those giants, they don't provide a contact. They only provide their useless postmaster tools.
They even warn you they will not give reasons about why you are rejected, when you can find some other useless form to fill in the endless loop of their documentation.
So not a good answer unless one can provide a real contact entry.

Maybe someone heard about an association or some initiative to try to deal with this annoying issue or a community who is trying to force them to provide an actual way to be recognized as legit, without to pay for being whitelisted.

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  • 3
    Your mail server may be suffering from a bad neighbors. The large players don't disclose their algorithms but they don't appear to rely on external black/white-lists (they probably receive such a large amount of mail they do that themselves). When you IP-address is not listed on those public lists that is not a guaranty that there is a no spam problem with (other customers of) your ISP and a complete address range may have been black-listed. I have had some luck with Office 365 (which possibly also improves delivery to more Microsoft services such as hotmail) sender.office.com
    – HBruijn
    Jun 11, 2019 at 8:11
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    Normally, this question should be closed as duplicate of serverfault.com/questions/48428 (yes!). Unfortunately, that canonical answer question doesn't really cover the issue you have. Also, since this is about your personal mail server, it's fundamentally OT here. But the fact remains that your problem gets ever more pressing for anyone that is not a big player and wants to handle it's own mail.
    – Sven
    Jun 11, 2019 at 8:55
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    Bad thing is: You can't do shit about it. Surely, MS and Google would deny they want to destroy small mail servers, but they definitively have no incentive to keep them alive either, and this situation suits them just fine, as more and more people are compelled to just use their services as the easy way out of the situation they have created.
    – Sven
    Jun 11, 2019 at 8:57
  • I started sending my personal email through Sendgrid some time ago, and no longer have deliverability issues. It's just too difficult to not be marked as spam sending to Google. Microsoft is a whole other beast; they will drop mail on the floor without notice, making them just too unreliable for anyone to use as an email provider anyway. I urge anyone still using them to go elsewhere, at least if they want to be sure they are receiving mail that people send to them.
    – Michael Hampton
    Jun 12, 2019 at 1:21
  • @MichaelHampton I'm sharing this feeling about Microsoft email solutions, but cannot really chose for other people, right? Sendgrid looks like an option but from a privacy point of vue I like the idea of operating my own smtp server. One point this question is raising being: is it still possible to own a mail server or are we screwed?
    – Stopi
    Jun 12, 2019 at 5:13

1 Answer 1

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I suspect @HBruijn is right and you have some unruly neighbours, which you can't fix. Here are some suggestions for moving forward.

Sign up to the mailop mailing list (yes, I know the cert is expired; the mailing list still works). This is a list for mail server operators which includes representatives from the big email senders and receivers.

Lurk for a month or so, and read a few months' worth of the list archives - there are usually several threads on deliverability problems each month. Implement the suggestions you see discussed (if you've implemented them already, double-check your configuration carefully instead), and if you don't get better results after a few weeks of running them, ask a well-researched question to the list. Don't do this without signing up to both the Microsoft and Google sender programs, reading through all their help material, and implementing their suggestions.

For me, the answers were:

  1. implementing DMARC
  2. keeping the volume low and not sending large batches of email at once

If you haven't done so already, it's worth signing up to a service like dmarcian and configuring your domain to send RUA/RUF emails to them so that you can view the statistics and configuration suggestions.

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  • OP has already said that no large batch emails (just few personal emails to legit contacts) and he / she respects DMARC. Just self-hosted personal email server. It is indeed a concern for self-hosted emails servers going forward.
    – Pothi Kalimuthu
    Jun 12, 2019 at 0:38
  • Thanks for the mailing list, I'll give it a try.
    – Stopi
    Jun 12, 2019 at 1:38

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