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.
I don't want a red queen scenario where if you go under 30 commits per day you explode, especially because it seems to hit both the long tail of low-resource off-beat projects and anything that interfaces with areas of society that benefit much more from being long-term stable. Besides the obvious infosecpocalypse of “update or get cracked”, what's causing this? Is there a way to turn this thing around, or some good ways to mitigate the effects?
I hope what you are saying about Win 10 is true. My organisation is in process of transitioning from Windows 7 to Windows 10 and things are breaking all over the place.
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.
Nearly everything that works in Windows 7 works in Windows 10, if you poke enough holes in it. The biggest exception to that is really just drivers, because hardware manufacturers have no incentive to update them past a certain point. There was definitely software that had to be updated to the latest versions to work, but that's where we needed to get to anyways.
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.
In my experience, Win 10 updates are still very much a crapshoot as to whether or not any given one of them will break something important to your org.
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.