Coming from Microsoft, this sounds like a privacy disaster waiting to happen.
Is this really something people have trouble with? Needing help to “figure out what to do next” on their computer? A lot of these AI features we are constantly seeing in the media sound like solutions in search for a problem.
I think the most compelling uses of AI are mostly “invisible” features (that are privacy-conscious, ie. data accessible by your devices only, and not the parent company) that improve existing services. Things like suggested map routes, better search and file organization, improved voice control and accessiblity, etc. But invisible features aren’t as marketable as big in-your-face features that I suspect are going to be more annoying than they will be useful.
I’d be willing to bet these “features” will mostly help Microsoft (and other companies who are jumping on this bandwagon) to serve you even-more-targeted ads. More cynically, it sounds like a great way for your government (or future government—people forget about this one) to spy on you even more than they already do.
UPDATE 5/22: The feature is called “Windows Recall” and this article on TechRadar echoes my privacy concerns.