Congress has long been concerned about the use of the Internet as an anonymous medium for the sale or exchange of child pornography.

In response, law-enforcement officials have maintained an aggressive posture through undercover operations to shut down a thriving illicit market that victimizes children.

But emerging technology is presenting new challenges to these enforcement efforts, particularly with the creation of "virtual" child pornography, images generated by computer.

On Tuesday, the US Supreme Court takes up a case that examines whether a 2003 federal law aimed at addressing the virtual child-pornography problem casts too wide a net that might also infringe constitutionally protected speech.

At issue in US v. Michael Williams is whether an individual can be arrested and sent to prison for a mandatory five to 20 years for attempting to arrange a swap of photographs that are believed to be illegal child pornography.

Under a 2003 child-pornography law, Congress empowered federal agents to arrest anyone for advertising, promoting, presenting, distributing, or soliciting material in a manner that is "intended to cause another to believe" that the material is illegal child pornography. The law applies even if the underlying material isn't actually child pornography.

US Solicitor General Paul Clement says the law, a section of the Protect Act, is a carefully calibrated effort by Congress to safeguard children from sexual exploitation by targeting those who would traffic in child pornography.

Critics say the law is a vague and overbroad regulation of free speech that threatens to establish the federal government as a kind of thought police. They say the government should punish illegal conduct, not controversial – or even repulsive – thoughts and fantasies. In addition, they say the law could chill artistic, literary, scientific, and other forms of protected speech.

"How are you as a promoter or as a describer supposed to know what is likely to make another person 'believe?' " asks John Feldmeier, a political science professor at Wright State University in Dayton, Ohio., who helped file a friend-of-the-court brief on behalf of the Free Speech Coalition, a trade association for the adult-entertainment industry.

The issue arises in the case of Michael Williams of Key Largo, Fla., who was arrested in May 2004 after an encounter with an undercover agent in an adult chat room on the Internet.

Mr. Williams logged into the chat room and posted a message that he had "good" photographs of his 2-year-old daughter that he wished to swap for similar photos. The undercover agent responded and engaged Williams in a private Web chat. The agent identified himself as a 30-year-old mother with a 10-year-old daughter.

Williams and the agent swapped photos. The children depicted in the photos were clothed and were not engaged in sexually explicit activities.

According to court documents, Williams tried to get the agent to provide a more sexually explicit photograph. When it did not arrive, Williams posted a warning message in the chat room that the undercover agent was a cop. The undercover agent responded in a chat-room message accusing Williams of being a cop.

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