I'm not sure about internal cultural reasons why but it seems like Microsoft just sucks at user experience for the most part, which is the key to the walled garden approach to me. I've never used a Microsoft product (other than mayyyybe the Xbox 360?) and thought, wow, this product is awesome and I'd never willingly switch to something else. You know, that feeling you get when you use something like an iPhone or Google products in the 2000s/early 2010s?