"Free riding" is not the right term here. It's more a case of being the angels in the saying "fools rush in where angels fear to tread".
If the industry as a whole were mature (in the sense of responsibility, not age), upgrades would be tested in offline environments and rolled out once they pass that process.
Of course, not everyone has the resources for that, so there's always going to be some "free riding" in that sense.
That dilutes the term, though. Different organizations have different tolerance for risk, different requirements for running the latest stuff, different resources. There's always going to be asymmetry there. This isn't free riding.