In Wooden v. United States, the Supreme Court held that a criminal defendant’s Sixth Amendment right to counsel was violated when his attorney failed to inform him of a plea offer before it expired. The petitioner in this case had been charged with possession of child pornography and entered into negotiations for a plea agreement with the government. His attorney did not tell him about an offer from the government until after it had already expired, leaving him without any chance to accept or reject it. The court found that this constituted ineffective assistance of counsel because his lawyer's failure deprived Wooden of “the opportunity to make an informed decision regarding whether or not he should accept [the] plea bargain." As such, they reversed and remanded the lower court’s ruling on Wooden’s conviction and sentence so that he could be given another chance at entering into a plea agreement if one is still available.

In Wooden v. United States, the Supreme Court held that a defendant's Sixth Amendment right to counsel was violated when he was questioned by police without his attorney present after being charged with a crime and having requested an attorney. The majority opinion found that the questioning constituted "interrogation" under established precedent, which requires Miranda warnings before such questioning can take place in order for it to be admissible as evidence at trial. Justice Alito dissented from this decision, arguing that there is no clear definition of what constitutes interrogation and thus no way to determine whether or not it occurred in this case. He argued further that even if the questioning did constitute interrogation, then any statements made during it should still be allowed into evidence because they were voluntarily given by the defendant despite his lack of knowledge about his rights due to inadequate legal representation prior to being questioned by police officers.