Outlook has stopped saving sent items

D Michael Enfield Said:

"Outlook has stopped saving sent items: [...]Suddenly, Outlook no longer places sent messages in the Sent items folder, or in folders designated by Outgoing Rules. The only way to find sent items is by using Spotlight."

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Remove the Outlook account, and then add it back.

Did you run First Aid on the Drive or...

Safe Boot from the HD, (holding Shift key down at startup), does the problem occur in Safe Mode?

Safe mode attempts to repair Disks & clears lots of caches, so if Safe Mode works try again in regular boot.

D Michael Enfield Said:

"My only problem now is locating any Sent email during those two days, other than by using Spotlight."

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Visit Your eMail Provider's Site:

Let's say you have a Microsoft Hotmail eMail address... If you go into your official account site, and log in there - is there any difference between that site and Outlook, particularly when it comes to items in the Sent folder? If so, remove the account, and then add it back. See if it all now syncs.