Thank you for the information Platonides. So, summarizing the events so far. 
There was a transfer to mailman 3 without consulting any local communities. 
Arguments like "a more modern look" and "convenience"  were used. The upgrade 
came and the persons responsible for the upgrade did so without fully releasing 
that there might be downsides or negative side effects. When people come 
forward with issue's regarding the upgrade not understanding what the issue is, 
the response is, take it up with Hotmail, the issue surely can't be the mailman 
upgrade. Microsoft should fix their stuff and if not, it's your problem. After 
asking for better arguments, an even more vague and technocratic story is told. 
I feel like I'm calling an insurance company, sigh. Thanks to Platonides, I now 
at least have a grasp at what the issue is. But this entire migration leaves me 
pretty unsatisfied. 
Regards,
Natuur12    On Sunday, June 6, 2021, 02:59:59 AM GMT+2, Risker 
<[email protected]> wrote:  
 
 You might also want to consider adding the mailing list to your contacts for 
Hotmail.  I have found this makes a big difference for Hotmail, even more than 
filters do.  

Risker/Anne

On Sat, 5 Jun 2021 at 20:16, Platonides <[email protected]> wrote:

First, I doubt you would get someone to change the hotmail filters. It's not 
like they added a manual rule. It works on autopilot. The spamfilter learns 
that such message is bad. Not even the Microsoft guys really know how it 
decides that. And even if the ip address was blocked, the technicians would 
just be allowed to "mitigate" the ip, and are not allowed to deviate from the 
runbook.
Second, the migration to mailman3 probably changed them enough so they "lost" a 
lot of the reputation it gained through the years. So if may have learnt that a 
message with certain wikimedia headers was ok, but mm3 emails are different 
enough they don't hit.
Third, mailman is sending spam messages to the list owners. Those are 
requested, but they are being sent, so hotmail does have a point. Do not mark 
them as spam, even if it is a spam sent to <list>[email protected], you 
want to receive them, not to make hotmail learn that email sent by 
lists.wikimedia.org is spam.
Mails blocked to the list and sent to the list owners are problematic (and 
spammy) enough that I think mailman should offern an option not to include the 
full email not passed to the list, but only the subject. But that'd be a 
feature request.In the end, if you are a list admin, you have requested to 
receive them, even if they are spammy. You should be able to configure your 
mail for that. However, you may be using a provider which doesn't allow that 
kind of flexibility.

By the way, gmail is marking me the previous mails of this list from Leon 
Haanstra as: "This message was not sent to Spam because of a filter you 
created." (they are not always obeying these filters ☹, but I am glad they at 
least allow them). This may be related to gmail considering list mail flow more 
spammy than usual, or simply because it's a yahoo.com email address and thus it 
fails the silly DMARC policy they added.

Regards
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