We (https://sjdm.org) had a different problem with Hotmail, but it
might be related. We are a nonprofit society with a couple of mailing
lists, one of which has over 4000 members from around the world. When
we moved to Linode (from my office desktop), we had many problems of
the sort that Stephen Turnbull described, particularly with our ipv6
address, but I won't discuss those because Microsoft uses ipv4.

Occasionally, every couple of months, we would be unable to send mail
to any Microsoft address. These included @hotmail (sometimes
hotmail.de or other countries), @outlook, @live and @msn, mostly the
first two. There is a complaint procedure here:
https://support.microsoft.com/supportrequestform/8ad563e3-288e-2a61-8122-3ba03d6b8d75
We went through it, but it didn't do much good. Usually the problem
would go away after a few days, but I now think that our complaints
had nothing to do with the problem going away. See below.

We also signed up for Sender Support.
https://sendersupport.olc.protection.outlook.com/pm/junkemail.aspx
and SNDS, e.g.
https://sendersupport.olc.protection.outlook.com/snds/FAQ.aspx
and https://sendersupport.olc.protection.outlook.com/snds/data.aspx
The last thing did list "complaints", but this did not seem to be the
problem. There were very few.

The typical message we got when our mail did not get through was this:

"Unfortunately, messages from [45.79.135.144] weren't sent. Please
contact your Internet service provider since part of their network is
on our block list (S3150)."

The problem is that we do not control "their network" except for the
single ipv4 address we use [45.79.135.144]. Microsoft may be looking
at other people who use Linode. Once I asked the Linode staff to help,
and they complained to Microsoft, explaining the situation, and it got
better for a while. I now think that their complaint had nothing to do
with the problem getting better. There was nothing else Linode can do
except try to monitor every one of their users for spam, and they do
not do that. I think that Microsoft may have a (much more expensive)
cloud service that works that way, but I am pretty sure that Amazon
Web Services does not. The Hotmail/Outlook problem comes and goes.

Occasionally, we would complain and get responses from what appeared
to be a person. I now think it was not a person, since the message was
always the same. Below is an example. That one came in the middle of a
block that lasted for a few weeks.

In the end, we decided to prevent users with Microsoft addresses from
signing up for anything, including membership in the Society. So far
we have received no complaints about that. All these addresses were
automatically removed from our mailing list by Mailman, in the last
outage, which was very long, and I did not put them back.

Our main mailing list has over 4000 members with almost 1000 different
domains. The only domains that ever block our mail are those
controlled by Microsoft, about 90 people (many who already signed up
with a different address and never unsubscribed their Microsoft
address). Usually every single post to our mailing list goes through,
except for occasional "user not found" and "over quota".

My opinion, FWIW, is that Microsoft should not be running an email
service of any sort. Verizon is shutting its service down (or already
did), and Microsoft should do the same.

#######################

Subject: RE: SRX1530278720ID - [EXTERNAL] Re: Reported deliverability problem to
        Outlook.com SRX1530278720ID
X-Mailer: Microsoft Avondale Mailer

Hello,

My name is Sai and I work with the Outlook.com Deliverability Support
Team.

We continue to look into this issue along with the Escalations Team. We
understand the urgency of this issue and will provide an update as soon
as this is available. Rest assured that this ticket is being tracked
and we will get back to you as soon as we have more information to
offer.

Thank you for your patience.

Sincerely,

Sai
Outlook.com Deliverability Support

-- 
Jonathan Baron, Professor of Psychology, University of Pennsylvania
Home page: https://www.sas.upenn.edu/~baron
Founding Editor: Judgment and Decision Making (http://journal.sjdm.org)
Associate webmaster: sjdm.org
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