This Note explores whether a condition of supervised release that restricts computer and Internet access violates the doctrine of unconstitutional conditions. Although a circuit split has developed regarding the scope of a permissible restriction, as Courts of Appeals have been inundated with cases challenging the validity of these technology restrictions, no court has yet viewed these limits through the lens of the doctrine of unconstitutional conditions. This Note begins with a discussion of the First Amendment and the theory of unconstitutional conditions, tracing their respective developments in cases relating to prisoners, speech, and the Internet age. Next, it synthesizes the oft-criticized idea of unconstitutional conditions into a new three-prong framework, judging the propriety of a condition based on the government’s coerciveness in making the offer, the purpose for pursuing the condition, and the condition’s effect on protected speech. Then, this Note surveys cases where courts have ruled on the validity of a computer or Internet restriction, and recasts their reasoning to discuss whether such a condition may be constitutional, using the coercion-purpose-effect framework. Finally, this Note concludes that a condition is constitutional where it is accepted knowingly and voluntarily, is intended to protect the public rather than regulate speech indirectly, and where computer-monitoring and Internet-filtering technology is maximized to minimize First Amendment infringement.