WHEN APPLE MAIL & GMAIL HATE YOU, and it looks like it’s going to send from the correct account – and the copy is in the correct account’s send folder, but the email recipient sees another email.
Problem: Infuriatingly frustrating. I sent work emails from Apple Mail and would get replies to my personal email. AGH GMAIL!
Solution: Change Your Outgoing Mail SMTP Account Info
By default when you add Gmail / Google Apps accounts, Apple Mail just stores the description as “Gmail”. When you have several “Gmail” accounts, it’s probably gonna get confused at some point, especially if you have deactivated or added new ones or made some / any change along the way. ie. Your new accounts may be using the first account you added to send out emails through. Gross, right?
See this diagram for solution:
1. By default, my outgoing server list read “Gmail / Gmail”. Wtf.. which Gmail do I use, they are all the same right? WRONG.
2. This isn’t really a step, just a note. My bad.
3. Rename the descriptions so they don’t just say “Gmail”
4. For each account description, click ADVANCED and make sure the AUTHENTICATING SENDER USER NAME / PW matches the email account you are trying to send through. MOST LIKELY, you’re trying to send email from susiework@gmail — but you’re unintentionally authenticating from your other private personal email account susiedarkside@gmail. OOPS. But because your susiedarkside info is correct, gmail accepts it, and both sends as susiework for YOUR records, but your clients see susiedarkside. OMFG.
5. If you can’t figure out which is which, just DELETE the email accounts altogether and start fresh. When you add your first, NAME the outgoing server description. When you add the second, NAME that outgoing server description. That way you can keep track.