In 2010, Pennsylvania man Anthony Elonis was convicted on five counts of transmitting threatening communications over the Internet for crude rap lyrics he wrote on Facebook threatening the murders of his estranged wife and even an FBI agent. Elonis has spent three years in prison, but is now seeking appeal from the Supreme Court.

Elonis has been defended by several free speech advocates, who say he is within his right to say these threatening things no matter how extreme his words may seem.

“The basic issue before the court is whether somebody can be found guilty of making a threat to another person if they did not intend to make that person feel threatened,” said Josh Wheeler, of the Thomas Jefferson Center for the Protection of Free Expression.

Ironically, though it may be within Elonis’ First Amendment rights to make these threats, they are in a direct violation of Facebook’s much-debated community standards, which allow individuals to say offensive things on the site as long as they aren’t targeted at individuals. Regardless, experts say, this case could prove to be a crucial opportunity for the courts to figure out how to litigate threats made on social media sites like Facebook.

“People use it to say all kinds of things but they may not be directing it to a particular individual. They’re just venting their feelings,” said Robert Richards, director of the Pennsylvania Center for the First Amendment. “It’s really time for the Supreme Court to sit down and develop a more rational approach to this.”