In the First Amendment-based speech cases of both Minnesota Voters Alliance v. Mansky in 2018 and Expressions Hair Design v. Schneiderman in 2017, Justice Sonia Sotomayor forcefully contended that the United States Supreme Court should have certified questions about statutory meaning to the highest relevant state court. This Article examines certification—its purposes, its pros, and its cons—in cases pivoting on whether ambiguous state statutes violate the First Amendment. Mansky and Expressions Hair Design provide timely analytical springboards. The Article argues that certification carries heightened importance today. That is because the justices now frequently fracture along perceived political lines over when a case involving speech merits heightened First Amendment scrutiny and when it deserves only rational basis review. This rift was vividly exposed in 2018 in both National Institute of Family & Life Advocates v. Becerra and Janus v. American Federation of State, County, and Municipal Employees. Although not a panacea, question certification might sometimes eliminate such splintering. The Article ultimately proposes four criteria for helping the Court to decide when certifying a question of state law in a First Amendment case is appropriate.