Hi Stephen,

Thank you a bunch for looking into this.

I was trying to say that ReplyTo: works fine, for just the reasons you mention. 
No problem there. At first. ;-)
But Apple Mail puts the mangled address To: into the ‘Previous Recipients’ list 
to help with auto-completion later.

Here are the steps. I’m avoiding real addresses, as my mail client further 
mangled them with the auto-inserted ‘mailto:’ command confusing my message.

Here goes:

a. Subscriber receives message from the list. The From: is a mangled From: as 
recommended, and the ReplyTo: is the author’s emal address:
        From: Author Name (author.address) via list <list.address>
        ReplyTo: author.address

b. Subscriber replies to author. Sees correct To: address (the author.address) 
from the ReplyTo: header. So far all is apparently OK.
However, to be ‘helpful’ with auto-completion later, Apple puts the mangled 
string “Author Name (author.address) via list <list.address>” into the mail 
client’s  ‘Previous Recipients’ list!! 
        To: author.address
        
c. Subscriber much later tries to send a private message to the author and 
starts typing "Autho...". Apple at this point retrieves the mangled string from 
the ‘Previous Recipents’ list, but in their infinite wisdom, they hide the 
actual address, which is the list address. The subscriber does not suspect that 
things have gone awry because it looks fine. Well, not completely fine, but 
enough so. So he/she hits ’Send’ while seeing this and only this in their To: 
field:
        To: Author Name (author.address) via list

d. People on the list receive a private message that was intended for the 
original author. Result: red faces all around and possibly private data exposed 
to the entire list. I just now happened to receive such a message from one of 
my lists! No real disaster this time, luckily, but confusing for the lists 
members. 

I do tell people to clean up their ‘Previous Recipients’ list, they eventually 
forget and this happens again.

If this can’t be solved somehow, I will have to unsub all my AOL and YAHOO 
subscribers (a lot), as it’s too dangerous to have the mangling causing these 
privacy mishaps. They don’t really have to change their main email, just get 
another one that they use only for the lists.

By the way, I have asked Brian to help with installing Mailman 3 and look 
forward to working with him and with the new system.

Yours,

        Allan
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