“Ought” implies “can,” and “We ought to regulate” implies “We can regulate.”
It is not always clear that we can.
This is a longtime theme/hobbyhorse of mine. Technology and other social changes will simply make it difficult or impossible to regulate some things that people with power would like to see regulated. Ban firearms, and we’ll 3-D print them. Ban books or movies, and we’ll still make and distribute them. That’s the technology end of things, but human behavior matters, too: Sure, the Internet and other communication technology has made it easier to buy and sell marijuana or to engage in prostitution, but mainly those things endure because people have decided in great numbers that they simply will not comply with the law — and, when people do that, it becomes very difficult to regulate.
For better and for worse, the people coming writing the software are smarter than the people writing and enforcing the laws.
The New York Times shares an account of Uber’s efforts to evade regulators looking to clamp down on its service. In short, Uber developed software to detect The Man in those markets in which The Man is trying to keep Uber down, making it difficult for The Man to use Uber and then file charges against drivers or impound their vehicles. It is a pretty amusing story.
How much law-breaking or law-evading is acceptable in the face of unjust or selectively enforced laws is a question for the philosophers. (At the moment, I could do without hearing anything at all on the subject from our friends on the left who believe that an acceptable response to political disagreement is committing acts of violence. Looking at you, idiot children of Middlebury.) But how much law-breaking and law-evading we ought to expect is a more down-to-earth question, and the answer is: quite a bit.
Most businesses and the vast majority of citizens are happy to comply with sensible and unburdensome regulation, just as most people are willing to pay their taxes when taxes are relatively low. But when regulation becomes cumbrous or punitive or when taxes become confiscatory, people and firms will evade them. That is not a normative proposition, only an observation of familiar human behavior.
There is a relationship between “Should we regulate?” and “Can we regulate?” As a practical matter, the question more often is: Do we prefer light regulation and high levels of compliance or heavy regulation and high levels of evasion? The NYPD has some very dedicated and intelligence men working for it, but I would not bet on them in a technological competition against an ordinary weed dealer with a cell phone, much less against the best minds of Silicon Valley.