I thought I was breaking the law. Okay, it was breaking the law in the dorkiest way possible, but still, breaking the law is always kind of cool (wait, I’m a lawyer — am I allowed to say that?). After hours of research, I put my brand new first generation iPhone into the hands of some rogue programming genius with a vitamin D deficiency. The plan was to jailbreak and unlock my iPhone. In simple terms, jailbreaking allows you to modify the iPhone operating system in ways that Apple doesn’t allow. At the time, the App Store was just a gleam in Steve Jobs’ eye; jailbreaking would enable me to download games and other apps iPhone owners now take for granted. But I was more interested in unlocking the iPhone, which would allow me to run the phone on T-Mobile instead of AT&T (and avoid AT&T’s ungodly rates). Somehow I wasn’t deterred by the dozens of horror stories online about failed jailbreaking attempts, stories about “bricked” iPhones that never worked again. I certainly wasn’t going to drop another $400 on a new iPhone, so I knew I only had one shot at breaking out of jail. I downloaded the program and, like magic, I was playing Super Mario Bros. 3 in a matter of minutes — never a doubt.

Apple has always contended that jailbreaking violates the Digital Millennium Copyright Act (DMCA). The DMCA prohibits the circumvention of technological measures which control access to copyrighted works. According to Apple, altering the iPhone operating system creates a derivative work which infringes on its copyright in the underlying code. The DMCA was enacted by Congress to prevent more traditional forms of Internet piracy (note: not traditional in the “yar, mateys” sense), but something like jailbreaking might technically be a violation of the DMCA as well — that is, unless the Copyright Office specifically exempts it from the purview of the DMCA, which it has the authority to do every three years. The Electronic Frontier Foundation (EFF), an organization dedicated to protecting the digital rights of consumers, asked the Copyright Office to do just that. And while federal regulators may be in bed with the oil industry — literally — they (wait for it) sure took a bite out of Apple! (Did I just hear groans emanating from across the country?)

Last month, we told you about the Copyright Office’s new special dispensation for circumvention of digital locks by documentary filmmakers. In the same populist decree, the Copyright Office agreed with the EFF, declaring that jailbreaking is “within the four corners of fair use” and therefore legal under the DMCA. In making its ruling, the Copyright Office pointed out that “the amount of copyrighted work modified in a typical jailbreaking scenario is fewer than 50 bytes of code out of more than 8 million bytes, or approximately 1/160,000 of the copyrighted work as a whole.” Not exactly the significant copyright infringement that Apple wanted us to believe. What the ruling really means is that the jailbroken iPhone collecting dust in my sock drawer is a perfectly legal circumvention of Apple’s security protections. I guess I can give up my old hacker pseudonym now (for those who might be interested, SuckItApple77 is now available).

The Copyright Office’s ruling hopefully begins to limit the DMCA’s anti-circumvention policy to the types of things that copyright law is actually supposed to protect. The EFF points out that the DMCA has been used to block aftermarket competition in laser printer toner cartridges, garage door openers, and computer maintenance services. Looking back, the idea that opening up the operating system on my iPhone would be a violation of copyright law seems (in the words of the great scholar Jackie Chiles) outrageous, egregious, preposterous.

But as some people just don’t seem to understand, the right to do something is not the same as the right to do it without consequences. Jailbreaking is still a breach of the iPhone user contract, so if Apple wants to take a page from the RIAA’s now-aborted public-relations-be-damned playbook, it can pursue breach of contract actions against individual users. Jailbreaking also invalidates the Apple warranty. For the vast majority of owners who are perfectly happy with Apple screening their apps, these deterrents will be more than enough, and Apple will continue to enjoy its lucrative closed business model and remain the (largely) uncontested master of its iUniverse. Although, because it no longer has the sword of copyright law available to it, Apple may to invest in developing security protections that, you know, can’t be routinely broken within a matter of days by the average high school-age nerd.

Now, for the more important issue — is it worth jailbreaking your new iPhone 4? While Apple’s own operating system has caught up with many of the features that previously made jailbreaking desirable, there are a few interesting features available for jailbroken iPhones. Two favorites: turning your iPhone into a WiFi hotspot, and running FaceTime (the iPhone’s incredible new video chat technology) over 3G. As for unlocking your iPhone to use a different phone carrier? I wouldn’t know — somehow, AT&T’s ungodly rates don’t seem so absurd now that the firm pays for my data plan.