Hello. I'm having this problem for a while now and did not find any topics about it on the net. If it is handled some other place already, the link, or way to find it would be nice. I'm using mail.app with 5 different accounts at work. Different accounts are supposed to be for different groups of receivers. When sending mails I unfortunately tend forget to check if the right sending address (account) is chosen. Mail automatically chooses the one from which the last mail was send. And so it ends up that people receive mails from the wrong address and are getting confused by that. Is there a way to make Mail always ask (some kind of pop up window, or so) from which account I would like to send the mail. After I pushed the sending button. Thank you for your help. PS: If the internet connection is disrupted for some reason such a window appears asking me which server (and therefor account) I would like to use. Edit the email, or telling Mail try it later again are the other options.