> when technology is designed in a way that makes it hard to work within the bounds of the legal system, it's usually the case that the legal system wins, not the technology.
If this was true, Internet pornography would have been successfully squashed by the existing obscenity laws that heavily regulated pornographic material.
It was, though? And continues to be. In the mid-90s, you could pretty easily find illegal material without looking too hard. It was already illegal by the Child Protection and Obscenity Enforcement Act, an early Internet bill which mostly said "illegal porn is still illegal, even if it's on a computer", and it also required producers of pornography to keep detailed records on talent & crew in the production. By the mid 2000s, large sweeps of enforcement happened, and thousands of studios without proper documentation and recordskeeping shutting down. The CIPA act required schools, libraries and public places where children could be to install internet filters, and make policies preventing children from viewing such material.
Pornography isn't illegal in the US, it's pretty well-regulated, and once the Internet started entering mainstream culture, it quickly adapted to the existing legal framework and culture that was already there.
This is, of course, a very US-centric view, but so is a lot of early Internet history, along with its culture.
I'm sorry, but this isn't true. At the early onset of the web there were a huge number of state and local laws regulating obscene material. Many states even tried to explicitly regulate Internet pornography:
> Between 1995 and 2002, almost half of the states were considering bills to control internet pornography, and more than a quarter of states enacted such laws.[1]
Along similar lines, sex toys were prohibited or heavily regulated in a number of US states before 2000. The technological reality of e-commerce means that the vast majority of the enforcement of those laws became impossible, and sex toys are de facto legal in every jurisdiction in America.
If this was true, Internet pornography would have been successfully squashed by the existing obscenity laws that heavily regulated pornographic material.