Congress has passed laws aimed at sexually explicit content on the Internet three times. Each time, opponents have brought First Amendment challenges to these laws, with varying success. In this Article, I argue that the third law Congress passed, the Children's Internet Protection Act (CIPA), which requires local libraries to filter Internet access in order to receive certain federal funding, implicates federalism as well as the First Amendment. My principal argument, found in Part III, is that the values of constitutional federalism suggest that the Supreme Court should have invalidated CIPA on federalism grounds but that it had no doctrinal tools for doing so. Such an approach would have provided a compromise result that would have permitted local libraries to continue to experiment with filters but would have simultaneously preserved public libraries' historical autonomy from federal control. In Parts IV and V, I then explore spending power doctrine and explain the historical origins and theoretical basis of a prominent proposal to change that doctrine in light of the new federalism. I suggest that changes to spending power doctrine could have led to the result I suggest but would not match my underlying constitutional policy rationales. Finally, I conclude with thoughts on the way viewing CIPA through the lens of federalism helps us better understand other conditional funding laws and also sheds light on the difficulty of crafting constitutional doctrine when both First Amendment and federalism concerns are raised by the same law.