Mail cannot send and remains in Outbox

Short story:
I [am trying to] have my SBCGlobal email in Mail. When I try to send messages all of the sudden, it just goes to the Outbox and refuses to send.
I even set up a Gmail account [IMAP] in Mail, and those messages also to go the Outbox.
I have tried booting in Safe Mode, repairing Permissions, removing a couple files (I forget which ones), which worked temporarily. But now I am right back to where I started.
Any ideas?
Thanks in advance! I really appreciate it!

Okay, well, it randomly started working. Then it doesn't work again.
It seems to work temporarily for no apparent reason.
Once it happens again I will let you know what Connection Doctor says. (right after it sent the messages successfully, it showed all connections are fine).
Thanks!

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