I know. A few years later, I was helping my mom set up a new laptop and during the same OOBE, I made pretty much the same comment, and she seemed to think it was just fine or at least not weird-sounding.
Come to think of it, I wonder if it's for the same thing that gets people to refer to Google Assistant/Siri/et c. as 'she'. I've noticed that a lot also.
It's normal behavior, we assign gender to all sorts of objects be they made of metal and float on water or are just a series of electrons informing metal gates.
The message is fine for the true target audience which is vastly different from the audience of the 80s and 90s. Microsoft and Apple (well, Apple HAS been using friendly language since the 80s!) are smart to use friendly language.
Plus, it gets us all used to our corporate god-kings when we're dominated by the AI angels.
Come to think of it, I wonder if it's for the same thing that gets people to refer to Google Assistant/Siri/et c. as 'she'. I've noticed that a lot also.