(NewsNation) — The U.S. Supreme Court will hear arguments this week in a case that could clarify which kinds of speech are protected by the First Amendment and which are considered a crime, particularly with messages sent via social media.

Billy R. Counterman is seeking to overturn his stalking conviction tied to Facebook messages he sent a woman over the course of several years.

Counterman’s one-way communication with a Colorado-based singer-songwriter landed him in prison for 4 1/2 years, but now he says that the reasoning behind Colorado’s law is flawed. That’s, in part, because it takes into consideration not only the speaker’s intent but the recipient’s interpretation of their speech.

What is the case about?

Counterman began messaging the singer in 2010. Although she never responded to Counterman and blocked him multiple times, she continued to receive messages from him under new accounts.

In some messages, Counterman claimed he’d seen the singer out in public. He told her to die in at least one message. Others included:

• “How can I take your interest in me seriously if you keep going back to my rejected existence?”
• “Five years on Facebook. Only a couple physical sightings.”
• “Was that you in the white Jeep?”
• “Your arrogance offends anyone in my position.”

The singer was granted a protective order against Counterman and canceled performances out of fear he might attend, according to court records.

After years of messages, police arrested Counterman in May 2016. A jury ultimately found him guilty of stalking and Counterman was sentenced to 4 1/2 years in prison.

Is it considered free speech?

Not all speech is protected by the First Amendment: This includes threats of violence or so-called “true threats.”

The Supreme Court defines true threats as “statements where the speaker means to communicate a serious expression of an intent to commit an act of unlawful violence to a particular individual or group of individuals.”

Counterman says the law he was convicted under makes it too easy to “criminalize misunderstandings.” That’s because in Colorado, a person doesn’t need to intend to carry out their threats.

“True threat” limitations also protect against the fear of violence, the state’s appeals court explained.

Counterman’s attorneys have argued that standard is “especially dangerous in the Internet age.”

“The notion that a person can spend years in prison for a ‘speech crime’ committed by accident is chilling,” his attorneys wrote in a February court filing. “Imprisoning speakers for negligently misunderstanding how others would construe their words is contrary to history, doctrine, and common sense.”

The singer’s family told ABC they’re worried about revisiting the past.

“It’s terrifying, honestly, to think that we might go back to a place where a victim might feel that they’re not going to believe me that this is truly threatening when clearly she felt that her life was at stake,” the signer’s sister told ABC.

What implications could the case have?

A ruling could bring more clarity to what is or isn’t considered a true threat, particularly in a politically polarized and chronically online world.

Groups like the Reporters Committee for Freedom of the Press and the American Civil Liberties Union have spoken out in support of Counterman’s arguments, but not necessarily his behavior.

The ACLU, for example, wrote that speech on social media can be highly political and accessible to a wide audience, members of which might interpret posts differently.

“As more and more speech takes place on the Internet, the constitutional protections afforded to online speech will increasingly determine the actual scope of First Amendment freedoms enjoyed by our society,” the ACLU wrote in a court filing.

The singer’s family, however, says she had a legitimate reason to be concerned about Counterman’s messages.

“We were convinced that he was an unstable individual and his actions would be unpredictable,” the woman’s sister told ABC. “We felt that he was very dangerous, and law enforcement agreed.”

The court is scheduled to hear arguments in this case on Wednesday.