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.
Almost everytime we change versions of software things break when we went moved to office 365 there was breakage (Stuff I would have thought for sure would have been well tested - PST files in outlook for example broke).
Same thing when we went from Internet Explorer 8 to 11 our internal intranet didn't work.
I work in an environment that includes custom-written apps from the Windows XP era, and usually the absolute worst we hit was "hey, this device doesn't work on Windows 10, we have to buy a newer one". Not a big deal when it's a $6 USB-to-serial adapter, but people will look at you like you're crazy when you say the network is incompatible with an HVAC system. (Solution in that case, just take it off the network, you're better off.)
But believe it or not, you can still sync Windows Mobile 2003 devices with Windows 10 PCs, Microsoft's backwards compatibility is still insanely solid in most cases.