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. When I write stuff in Word, Word seems very opinionated and messes up formatting all the time. Saving things to our disk is also an ordeal because they are pushing OneDrive.
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. When I write stuff in Word, Word seems very opinionated and messes up formatting all the time. Saving things to our disk is also an ordeal because they are pushing OneDrive.