Yes I think it is just a Microsoft programming bug that they are unable or unwilling to fix. I did find a solution (if you would call it that). In Indexing Options, Indexing Options> Modify - un-check Microsoft outlook. That's right un-check it. Search then works. Microsoft Outlook will tell you there is a problem when you do search and it that it cannot search but it actually does. (for me anyway).



I wish Microsoft would fix their bugs - they go on about how amazing there software is an then cannot even solve an mail index search problem.

My Outlook 2016 search stopped working sometime back in March due to a some Office 2016 update or another. I had to roll it back to an earlier version and then disabled updating until MS came out the fix.

All was fine but I forgot to re-enable Office updates until yesterday. Downloaded all the updates that had come out since March. Search still didn't work and returned the dreaded "Something Went Wrong" error message. Apparently on account of some recent windows update this time, Lol. I had to un-check outlook indexing for a temporary workaround. This is all starting to get a little ridiculous.