On Monday, September 12, 2022 at 16:25:12 -0400, John Hawkinson wrote:

Mihai Lazarescu <mtl...@gmail.com> wrote on Mon, 12 Sep 2022 at 15:07:37 EDT in 
<yx+dedsraermd...@lazarescu.org>:

> It took some work to set it up, but that's it. Surely not a mass solution, 
yet feasible and stable.
...
> Only Microsoft (outlook.com, hotmail.com) seem to filter the whole IP block, 
but I am too lazy to ask the provider to fix or change provider altogether.

This is hard to take seriously. Precise numbers are hard come to by, but I 
think Microsoft is the number 2 hosting provider, globally, after Google/Gmail, 
and has a substantial market share. Deciding that it's OK to not worry about 
them suggests a very different attitude toward email reliability and 
interoperability than most people would choose.

I never claimed that my specific case is universal:

1. I only have one contact on Hotmail and then I can use Google SMTP. I had my domain registered for use on Google Workspace (or whatever was the name earlier) long before I switched to the homegrown. And I still keep Google as safeguard if something-tragic-happens with my servers. For work contacts on Microsoft servers I use the work email (also on Microsoft).

2. The IP-block-on-antispam-lists is just an issue of the current provider (a convenient $12/y, checked it in the meantime). No issues before this provider. Nevertheless, this should be checked, and/or seek contractual guarantees, and/or be prepared to switch on short notice. Or use reputable email hosting providers, as someone mentioned earlier.


That being said, I found at work that Microsoft uses a very crude spam filtering (kind of 1980s database-driven). E.g., it indiscriminately junks all messages from almost any mailing list I join. Moreover, if I un-junk the messages, Outlook behind the scenes whitelists the *sender address*, not the list address/ID. Thus:

- I've got myself a never ending job to move legit messages out of the spam folder for every new sender seen on lists

- I end up with a huge whitelist of people I don't personally know

- if I go and clear the Outlook-built whitelist, the spam filter behavior resets: all messages from the lists are junked, etc. (hence my strong feeling that it's db.whitelist-driven).

Besides, at the switch to Microsoft systems the sysadmins strongly advised to carefully check the junk folder for important messages. And I also found that Microsoft junked its own automated notifications, e.g., for OneDrive shares. Go figure…

In 2022 I find astonishing how much of Microsoft's antispam seems to rely on lists (addresses, IP blocks…). Leading to annoying false positives, with rates well higher than Google's. Microsoft's antispam filters may very well include some well hidden adaptive smartness, though. ;-)

Best,
Mihai

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