This year, state legislators updated Massachusetts' "Crimes against chastity, morality, decency, and good order" law which previously prohibited obscenity in printed or handwritten form. It now also includes indecent matter in electronic forms, like e-mails, instant messages and text messages. In fact, the law gets even more specific, and includes any writing, images, sounds, data or intelligence that is created or transferred by computer, telephone or "any other device" that's transmitted in whole or in part by a wire, radio, electromagnetic, photo-electronic or photo-optical system.

Though these changes were approved back in April, the date the updated law went into effect came at an interesting time -- within days of the U.S. Court of Appeals for the 2nd Circuit deemed that the Federal Communications Commission's indecency policy was "unconstitutionally vague," potentially promoting self-censorship of material protected by the First Amendment.

While a federal appeals court ruling is moving in one direction, it appears that the Massachusetts provision might be a step backward. The state's updated law is certainly causing a stir among many organizations, including the American Civil Liberties Union, who are suing to block the Massachusetts law claiming it, too, violates free speech -- and say its lines are rather blurry. "Due to the very nature of the Internet, virtually every communication on the Internet may potentially be received by a minor and therefore may potentially be the basis for prosecution," the complaint says.

But ultimately this update was made for a good cause: to protect children. "It was actually our case here in Plymouth County that I think probably got the whole thing going," says Plymouth County (Mass.) District Attorney Timothy Cruz, speaking of the Commonwealth vs. Matt H. Zubiel case. "A few years ago, we did online undercover stings with deputy sheriffs and state police posing as 13-year-old children. It was a big operation called Operation Trenchcoat."

In one particular case in 2006, Deputy Sheriff Melissa Marino of the Plymouth County, Mass., Sheriff's Department High-Tech Evidence Analysis Team created an undercover screen name, "Melissa QT 1995," and set up a Yahoo profile. This profile stated that she was "Meliss Smith," a 13-year-old 8th grader from the South Shore, and invited others in the general discussion to "PM" her if they would like to send her a "private message."

"As soon as the undercover [officer] would call himself either a 13- or 14-year-old child who obviously was in the wrong place and shouldn't be there, the majority of people would leave and not talk to that person," Cruz says. "But other individuals would stay online and have relatively sexually charged conversations with whom they believed to be a 13-year-old child. And many times it wasn't unusual for them to send pornographic pictures."

Four private IM conversations occurred between Feb. 8, 2006 and Feb. 17, 2006, in which Zubiel, age 25, knew Marino was 13 years old and still brought up several intimate topics, including her physical appearance and sexual experience. When the two arranged to meet on Feb. 18, 2006, police arrested him upon his arrival to what he thought was Marino's apartment.

"He was charged with a number of criminal complaints at that time, including the allegation as set forth in 272, section 31 [the decency law], the attempt to disseminate matter harmful to a minor," Cruz says. "He subsequently was charged in court; he had a trial in court; he was convicted; he was sent to jail."

But his case went up to the state's Supreme Judicial Court, which determined in February that the definition of the word "matter" did not encompass online electronic transmissions. "So for a short period of time in Massachusetts -- before it got changed -- as long as you weren't sending videos, as this was strictly language, you could send electronically charged language to people you thought were children and you couldn't be prosecuted," says Cruz.

In essence, online conversations were technically legal, but if you printed that conversation out or wrote the same language out by hand, that was illegal. Because online conversations were the basis of the case -- and online verbiage did not count as "matter" under the law at that point -- Zubiel's convictions were overturned.

As a result, the law was changed -- but the law's line is thin. Opponents of the updated law argue that this new addition bans anything on the Internet that may be considered "harmful to minors." This technically includes material adults have a right to view under the First Amendment, such as various types of art and literature, and information about sexual health, pregnancy and contraception, to name a few. Individuals with zero intention of enticing a minor by sharing such art, literature, or health information fear that they run the risk of doing so unintentionally, and could potentially be prosecuted.

Because Cruz has not yet been officially served with the lawsuit, he cannot speak to how he will respond to the charges -- or whether anyone unintentionally "showing" a minor indecent matter would be prosecuted.

"What I am saying, and what I think other DAs are saying, is that our job is to protect children in our communities," he says. "Many times I think we find ourselves banging square pegs into round holes because the laws, when they were originally put together, did not encompass or foresee the Internet."