When Outlook won't send messages, I've snooped around looking at the task manager and have seen two instances of Outlook running. Only one is visible on the screen or in the taskbar. I suppose each is waiting for the other to act in a responsible way. So I bought a $5 shareware add-in program called Outlook Shutdown. If you shut down Outlook, it shuts down it's hidden cousins also.
When I'm going to be away from my computer for awhile, I use ZoneAlarm's Internet Lock to keep vandals away. If Outlook is running, it will never ever be able to send or receive an email again. It's that stupid! I have to shut it down and then reload it.
On Monday something very suspicious happened. Outlook on two computers got a "Microsoft is sorry" screen and I kept clicking until I got to what appears to be a heavy-handed attempt by Microsoft to get you to upgrade:

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