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Today the Supreme Court took up a very difficult question: if a person explains to a terrorist group how to pursue peaceful resolution of their goals, is that constitutionally-protected speech?

Federal law, as amended by the USAPATRIOT Act, makes it a crime to provide “training” and “expert advice or assistance” to designated terrorist groups. The Humanitarian Law Project (HLP) in years past provided advice to groups including the Kurdistan Workers’ Party (PKK) and the Liberation Tigers of Tamil Eelam (LTTE), both groups designated terrorist groups by the State Department. HLP trained the groups on using international law, including petitions to the United Nations, to achieve their goals peacefully. HLP says the groups formed to protect the rights of minority populations that they argue have been marginalized, and HLP sought to help the groups move away from terrorist tactics and achieve their goals through peaceful means.

The Obama administration, however, argues that providing aid—including legal advice—to the groups would run afoul of federal law. Solicitor General Elena Kagan, who represents the federal government before the Supreme Court, argued today that aiding these groups helps them achieve legitimacy, and the government not only seeks to stop their terrorist activities, but also wants to dissolve the groups themselves. Moreover, the government argues helping the groups with any one aspect of their operation frees up personnel or gives them more time to pursue terrorism. Thus, any aid to these organizations is in effect helping them carry out terrorism, and since terrorism is an action and not speech, the First Amendment to the Constitution does not protect the aid groups.

Justices subjected both lawyers to tough questioning. Conservative Justices John Roberts, Anthony Kennedy—usually the swing vote in close cases—and Sam Alito all seemed skeptical of the contention that the aid HLP wanted to provide would not help the groups carry out terrorist attacks. They also seemed hesitant to accept the government’s argument that the line between “advice” and “expert advice” was clear; advice is legal, while expert advice is not. One point of agreement seemed to be that there was a problem with any law that might make it illegal to provide legal advice.

The lawsuit was brought as an “as applied” challenge, meaning HLP was asking only for a declaration that its activities were protected, not that the whole law be struck down, but there seemed to be much confusion about how the Court could make such a declaration without imperiling prosecution of anyone under the law. That confusion may provide an out for the Court: it could send the case back to the lower courts for consideration of whether the law is unconstitutional entirely.

The case, Holder v. Humanitarian Law Project, will be decided before this summer.