I examine whether the Supreme Court may reconsider laws regulating virtual child pornography as AI-generated deepfakes become more realistic. Although real child pornography is illegal, prior federal attempts to ban simulated depictions were struck down on First Amendment grounds in Ashcroft v. Free Speech Coalition. I argue that advancing technology may justify revisiting this issue, as distinguishing real from artificial content is becoming harder. Carefully tailored regulation — such as labeling requirements or proof no minors were involved — could protect children while respecting free speech, making renewed federal legislation increasingly likely.