I have multiple accounts linked to my Gmail.com account, so that when I click Compose in the web app, I can choose one out of a few "From" addresses.
Is there a way to make it pick a "From" address that has the same domain name as the recipient if there is one available?
Basically if I fill in a recipient, say jdoe@mycollege.edu, it'd automatically pick me@mycollege.edu as the "From" address.
Best Answer
It used to be possible as long as you could verify the email Google sent to the reply email address you were adding. However, now Google won't allow you to send from a domain other than gmail unless you have a Gmail business account, or you can use SMTP auth.
If you have a user name and password for the SMTP server of the domain you want to send from, you can use that.
I spent quite a while trying to work around this issue, including using outlook.com SMTP server and an outlook.com alias for the domain I wanted to send from, but the reply address was always the original outlook.com address.
There are services like http://www.authsmtp.com/, but I haven't used them, so I don't know if that would work or not.