Legal scholars on both sides of the issue have raised flags. On Twitter, Katherine Franke, a professor at Columbia Law School who sits on the Academic Advisory Council of the pro-boycott group Jewish Voice for Peace, called the order “clearly unconstitutional.”

Eugene Kontorovich, a professor at Northwestern University’s Pritzker School of Law, who has supported anti-boycott legislation, has suggested that Mr. Cuomo’s executive order could run up against the First Amendment, and that its language penalizing advocacy of boycott or divestment — the measure is aimed at those who participate in pro-boycott activity or “promote others to engage” in it — was “a bridge too far.”

In analyzing a similar law passed in South Carolina last month, The Harvard Law Review wrote that the motivation behind such laws “could not be more antithetical to the core values of the First Amendment.”

Worse yet, the vagueness of Mr. Cuomo’s executive order raises more questions than it answers. For example, as the owner of a small web-design business who occasionally does freelance work for CUNY schools and state agencies, will I be denied contracts because I argued against buying SodaStream home carbonation systems while they were being manufactured in a settlement on the West Bank? If a filmmaker declares support for boycotting Israel, will the state deny her production company access to shoot at the new state-funded production center near Syracuse? If a church’s national assembly backs divestment from Israel, will it be denied state grants to operate homeless shelters and soup kitchens in Brooklyn?

And what about companies working in the West Bank that succumb to the economic pressure of boycotts or divestment and move their operations? Will the State of New York tell a private enterprise that it must choose between losing money because of boycotters or losing contracts with the state?

But this is also personal. As a Jew who has lived in Israel and has many relatives there, I feel that the government should not be dictating how I relate to the Jewish state and in what ways I voice my objection to its policies. Regardless of how one feels about the Israeli occupation and the B.D.S. movement, Mr. Cuomo’s decision should be an unsettling precedent.