There is an issue where if you close Outlook via the Red X in the corner, it doesn’t close the same way as doing so via File/Close. This affects all versions of Outlook, btw. The X was hanging and leaving the exe process running as a background task, which, if you disconnect the computer, (laptop) causes issues.
Solution: disable the iTunes Add-in or any other Add-in that is unneeded.
At least it seems to be working…
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