This conversation has been merged. Please reference the main conversation: How do I set up IMAP email in Mac Mail (OSX Mavericks)
What does this mean - should I be worried? This happens every time I try to send an email. It began when Homestead changed email providers. "The certificate for this server is invalid. You might be connecting to a server this is pretending to be "smtp.homestead.com" which could put your confidential information at risk. Do you want to connect to the server anyway?"