Mail Act On will do this. I have no idea if it is accessible, I looked at the 
product about 7 years ago when I was doing some consulting. 

Besides conrolling outgoing messages, one can set up pseudo smart actions to 
file messages. 
http://www.indev.ca/MailActOn.html 

Let me know how it goes.



Jonathan Cohn 

> On Aug 24, 2015, at 8:27 PM, Alex Hall <mehg...@icloud.com> wrote:
> 
> I thought not. One thing I'll mention, in case anyone else wants to do this, 
> is the tip I found on a forum. Mail will set your outgoing address to match 
> the current message or mailbox. So, if you set each of your accounts' inboxes 
> as a favorite, you could press command along with the number to bring up the 
> mailbox of the account you want, then press cmd-n. Mail will set your address 
> to match the account in use. Not perfect at all, but it's the only thing I 
> found. I think you also have to enable the setting to match the current 
> message account, so if you have that off, this won't work.
>> On Aug 24, 2015, at 7:20 PM, Matthew Dierckens <matt.dierck...@me.com> wrote:
>> 
>> I don’t think you can do this automatically, just change it in the window 
>> every time, unfortunately.
>> Hi Alex,
>> 
>>> On Aug 24, 2015, at 7:08 PM, Alex Hall <mehg...@icloud.com> wrote:
>>> 
>>> Hi all,
>>> I've looked into this, and there appears to be no way to do it, but I 
>>> wanted to double check in case someone here knows something. I want to be 
>>> able to have Mail on the Mac change the selected email account for a 
>>> message based on whom I am sending the message to. For instance, if it goes 
>>> to a certain address or group, my Gmail address will automatically be used 
>>> instead of my default iCloud address. A way to do this would be great, but 
>>> it looks like there's not only no way to do it in Mail by default, there's 
>>> no way to script it. Has anyone come across anything like this? Thanks.
>>> 
>>> --
>>> Have a great day,
>>> Alex Hall
>>> mehg...@icloud.com
>>> 
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> 
> 
> --
> Have a great day,
> Alex Hall
> mehg...@icloud.com
> 
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