Part I of this Note will discuss the current sentencing scheme in the federal system. It will discuss the goals of sentencing under the U.S. Sentencing Guidelines (the “Sentencing Guidelines” or “Guidelines”) and the discretion given to judges in imposing appropriate sentences, as well as some procedural safeguards. Additionally, Part I will discuss the process of supervised release, including how judges impose conditions and the process for revoking supervised release if a probationer violates a condition. Part II of this Note will discuss the circuit split over the imposition of a general ban on legal adult pornography. Finally, Part III of this Note will discuss the advantages and disadvantages of requiring district courts to give a sufficiently specific definition of pornography when setting conditions of supervised release. Also, Part III will provide a specific definition of pornography that satisfies the Supreme Court’s vagueness concerns in Grayned and will show how this definition properly balances the rights of the probationer—namely, the right to conditions that are not vague—with the goals of supervised release—ensuring public safety and furthering the probationer’s rehabilitation.