I believe some around 2000 Office and Windows reached their peaks of usability. They seemed to designed to get stuff done. Since then it seems they crammed more and more "intelligent" functions into the software that made them less predictable. I still don't know under what circumstances Windows Search finds things sometimes and sometimes it doesn't. Lately Outlook search feels random. Teams search is a complete mess…
Between my two work computers, I have different versions of outlook and between the two, Microsoft seriously screwed up the search.
Though I don't have issues with the windows search, maybe because I don't search inside the files (I don't use windows search to do that)?