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What a waste of a morning! A customer called early and mentioned that they could not reply to an email I had sent yesterday. It was trying to send to an email account that I closed over a month ago...but that wasn't the account that I sent it from...WTE? I went to my Sent Items and sure enough, they show with the old email address, not the outlook.com account that it clearly showed when the email was being composed. I checked all the account settings and all seemed to be correct. An hour and half a dozen test emails later, it appears that Outlook was using the old alias for my Microsoft account, not the new and correct one which had been set as the Primary over two months ago! I deleted the old alias and now it works. Thanks MS for changing the 'from' address for me! What was I thinking?
The first time I tried to set up outlook (older version) I found out to late that the default setting (buried real deep) was to delete all mail from the server.
At the time there was not a way to recover them.