I have recently set up my Mac Mail as an IMAP account using Google as the server, Gmail. I also had a POP account set up in my Mac Mail using the same Gmail account. I deleted the POP account because I preferred the IMAP account and I only require one account. When I deleted the POP account my Mac Mail no longer was receiving and sending mail the way it did before I deleted the POP account. The part that is confusing is that my Gmail's account settings had disabled the POP and enabled the IMAP. In another words when my Mac Mail was working is working with only the IMAP enabled in the Gmail account settings. Since then I have deleted the origianl POP and IMAP accounts to start over. The problem is that my IMAP account in Mac Mail receives and updates me exactly the way it should, but I am unable to send. I went to the connection doctor and the incoming server connects great it is the outgoing server that will not connect and when I try to send any mail my smtp server times out on port 0. I have the port set on 993 my NAT has port 993 opened as well as 587, Nothing outside of Mac Mail has changed when Mac Mail was working correctly, but my new IMAP account will not send any mail, why? And how do I fix this problem? Thank you very much for taking the time to help.