What do you mean exactly? Like the Menu-Issues in Windows 10?
Because from a UX perspective, basically nothing has change. UI of course, but UX is the same like in the 90's following "The Design of Everyday Things" by Donald A.
I think its more about the change management, expectations. For example in Win XP you had the option to use the NT theme. As a user: "I can decide when to move on to the new design."
Usually around 50% of your users are conservative about change. You have to keep this in mind when u change design.
On the other hand, if you sell a product with subscription, you have to introduce new feature, else user will move to another product. But, when you introduce new feature, UI gets more complicated and user will blame you for that.