I'm not sure it's as bad as you think. The cell phone industry and the carriers are the ones who built the jail, and the inmate is you. It is probably worth making sure that nuance is communicated, but it's a powerful image. If you're not a criminal, why are you in jail?
But why would you think like that? If, outside of any smartphone connection, someone said they'd "jailbroken" I would think "they were in jail", not "I wonder if they deserved to be there".
If you call yourself a jailbreaker you a describing yourself as an escaped criminal to many people.
> It is probably worth making sure that nuance is communicated
We live in an entirely nuance-free culture. We have an electoral campaign where candidates are being attacked for speaking basic French. Where an electorally significant percentage of the population believe that Saddam Hussein was responsible for 9/11 and that Barack Obama is secretly a Muslim.
When the US government is unable to successfully impart basic factual knowledge, basing a political campaign on anything with the slightest element of ambiguity or nuance is madness.
A friend of mine started working at the Hacker Dojo in Mountain View. He was working on a web app with his brother, who was actually in another country.
Shortly thereafter, he gets a very worried call from his brother, saying "We've been hacked!" He saw a lot of traffic in the logs from an IP connected with the word "Hacker" and got a bit panicked.
I'm a Hacker Dojo member, and I can relate. I check into the Dojo on Facebook and I always have a few people who think I'm doing nefarious things like "hacking" people's Facebook account. I've been pretty good about educating people about what hacker's actually do, or at least this hacker so the questions have gone down to a minimum as it seems they're bored with the reality.