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 <[email protected]> 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
> [email protected]
> 
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