I guess if the original design was flawed enough to begin with, then obviously people catch up on proper redesigns a lot easier since any good UX work will naturally make them feel more understood by the product.
Win3.11 to Win95 springs to mind here.
In contrast, going from "good UX" to "better UX" is a whole different endeavor since you'll have to fight against the friction of people having to give up routines and flows that they have been sticking to for a long time. A thing which no amount of thoughtfulness and consideration of a redesign will be able to make up for – that is, initially.
Win3.11 to Win95 springs to mind here.
In contrast, going from "good UX" to "better UX" is a whole different endeavor since you'll have to fight against the friction of people having to give up routines and flows that they have been sticking to for a long time. A thing which no amount of thoughtfulness and consideration of a redesign will be able to make up for – that is, initially.