Hi Jayson,

> ... This makes me think she's doing something to cause a complaint to be 
> generated, and doesn't realize she's doing it. ...

We get a fairly steady stream of these "complaint" messages from 
"staff[AT]hotmail". They don't seem to amount to much and I'm guessing they're 
simply a result of people leaving messages in their junk folder (where they've 
been delivered automatically).
 
> 1. Is Linode, my VPS provider, also receiving these complaints? If so, I'm 
> surprised they haven't at least sent me a notice telling me about them.

The "complaint" messages that we receive are addressed to 
"postmater[AT]the.sending.servers.domain". They don't appear to be BCCed to the 
hosting company.


> 2. Does anyone know if having received these complaints might cause Microsoft 
> to be more likely to add my IP to their infamous block list? ...

Quite possibly it does. Once or twice a year Microsoft will block our list 
messages. The log files will show that our server is on their network block. 
The process is then:

A. Check that ALL your DNS records are in order (double check your DMARC, DKIM, 
SOA) and that your IP isn't blacklisted anywhere: https://mxtoolbox.com

B. Check that your server's IP reputation is okay at: 
https://talosintelligence.com

C. If you're all good with A and B, complete Microsoft's de-list form - 
https://sender.office.com

D. Your request will generally be refused initially so you need to reply 
(sometimes more than once) and explain that all your records are in order, the 
nature of your list, subscribers are double-opt in, and the measures you have 
put in place to prevent spam being sent.

E. I've found them to be responsive and generally there is a positive result 
within a day or two. 


/Mark
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