US v. Poindexter: Poindexter pleaded guilty to three counts of distribution of heroin after beginning trial. He entered into a plea agreement with the Government in which other charges were dropped, the parties agreed on the amount of drugs attributable to Poindexter, and Poindexter waived his right to appeal his sentence unless the district court upwardly departed or imposed a sentence above the statutory maximum. Poindexter received a sentence within the Guideline range and did not appeal. A few years later, Poindexter files a habeas petition under 2255 alleging ineffective assistance of counsel. Specifically, he argued that he told his trial attorney to file an appeal and the attorney did not do so. The district court denied Poindexter's claim because of the plea agreement appeal waiver.
On appeal, the Fourth Circuit reversed. Applying Roe v. Flores-Ortega, 528 U.S. 470 (2000), the court held that when a defendant tells his attorney he wants to file an appeal, the attorney is under a duty to do so. Because the district court failed to hold a hearing to determine whether Poindexter actually made such a demand, the case required remand. The court rejected the Government's argument that the appeal waiver had any effect on that holding, noting that such waivers do not prevent the filing of appeals and the Government is free to rely upon it when fighting the appeal.