This really is the honest truth, every interaction I have with the MS platform is somehow worse than an actual dumpster fire. AI is the only thing keeping the ship afloat. Then again maybe that's the point?

I have the pro Microsoft copilot subscription at work just so I can search Outlook and teams since the native search doesn't turn up things when I search exact strings that are in the messages or use filters for other things like sender or recipient. Crazy to have to use an llm just to find an email

I'm so deeply perplexed by how bad Outlook search is

The "Advanced Find" in pre-2016 versions of Outlook was superb. Then it was "de-emphasized" for the crap search that followed.

Especially when they bought a superb product just for searching Outlook (LookOut), incorporated it into Windows Search and somehow destroyed it in the process.

Did you make the mistake of enabling the "new" (web-based) outlook? At least AFAICT, the "classic" one hasn't regressed much/at all

I used legacy relatively happily when I had a windows laptop, but recently switched to a MacBook and it either forced migration or was already the new version (don't remember). The macos outlook is a bit borked too. Beyond the typical level for outlook. Can't create or edit rules anymore that save to server. Need to go into the web version via browser.