I don’t know about hotmail/msn specifically but Yahoo and AOL (if AOL actually 
still exists!) are notorious for deciding for a user that something is spam and 
generating a complaint. I know I’ve seen similar issues on another list I 
manage (not using mailman, though)

On Apr 6, 2022, at 3:40 PM, Jayson Smith 
<jayb...@bluegrasspals.com<mailto:jayb...@bluegrasspals.com>> wrote:

Hi,


I run a relatively low traffic Email list on my VPS at Linode. Twice within the 
last two weeks, I've received an Email from 
st...@hotmail.com<mailto:st...@hotmail.com> with the subject "Complaint about 
message from XX.XX.XX.XX" where XX.XX.XX.XX is my IP. I'm signed up for 
Microsoft's Junkmail Reporting Program, and this is the first time I've ever 
received a complaint from them. Using message headers, I've identified the 
complainant to be the same list member both times. The actual Emails from 
st...@hotmail.com<mailto:st...@hotmail.com> have nothing in the body, and the 
complained about message as an attachment.


Obviously I can't have complaints tarnishing my Email sending reputation, so I 
contacted her to see if she was legitimately marking messages as spam/junk, or 
was doing it by accident, etc. Her response is that she has never marked any 
Emails from my list as spam or junk. In case it matters as far as the user 
interface goes, her Email address is at the msn.com<http://msn.com> domain. 
Obviously *something* has to be causing complaints to be generated, so if she's 
not doing it, what could be causing this? Are there any automated processes at 
Microsoft that could cause a complaint of this type to be generated? Is she 
somehow marking messages as spam or junk without realizing it?


Thanks for any thoughts,


Jayson


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