A huge upside of Windows 10's six month rolling releases is that they initially broke a lot of badly written things, and software and processes have had to improve to handle them better.

The end result two years later is OS upgrades rarely break much, and regular updates never do. Enterprises can be unstuck but it can be painful.

I think enterprises are still shifting from the old approach where you make it work and then it's fine, to realizing that in an internet-connected world, you have to keep up at all times. A few big liability cases would do wonders to push this shift along.