It is common for federal defendants to prospectively waive a broad swath of appellate rights when agreeing to the terms of a plea bargain, including any claims of ineffective assistance that may arise from their attorneys’ conduct at a future sentencing hearing. However, the argument has developed in recent years that such an agreement may present a defense attorney with an impermissible conflict of interest, which in turn prevents the attorney from providing reliable counsel to the client with regard to the agreement’s terms in violation of the client’s Sixth Amendment rights. In essence, this attorney is being asked to counsel the client as to the quality of his own future conduct. As such, many state ethics boards have concluded that these prospective waivers violate one or more rules of professional conduct designed to preserve a defendant’s right to reliable and unconflicted advice. In contrast, all federal circuits continue to enforce the validity of these waivers, as virtually any right may be knowingly and voluntarily foregone in a criminal prosecution. However, no federal circuit court has fully considered what effect this alleged conflict of interest may have on the agreement’s enforceability. This Comment asserts that federal courts must thoroughly assess the alleged conflict under the existing framework of conflict-of-interest law in the criminal context and ensure that these waivers are executed in an ethical and professional manner so that defendants’ Sixth Amendment rights are upheld in all instances.