In the 1988 case Penson v. Ohio, Steven A. Penson appealed his conviction for multiple counts of rape and kidnapping on the grounds that he was denied effective assistance of counsel during his appeal process. His court-appointed attorney had filed an "Anders brief," stating that there were no valid legal arguments to be made in favor of overturning Penson's conviction, and subsequently withdrew from the case without being replaced by another lawyer. The Supreme Court ruled unanimously in favor of Penson, holding that this situation violated his Sixth Amendment right to counsel because it left him without any legal representation during a critical stage of prosecution - namely, the appeals process. The Court also noted that even if an Anders brief is filed correctly (which they found wasn't done here), a defendant still has a constitutional right to have their claims reviewed by some form of counsel before deciding whether or not those claims are frivolous.

In the dissenting opinion for Penson v. Ohio, Justice Scalia argued that the majority's decision to create a new rule requiring automatic reversal of conviction when counsel is denied at sentencing was unnecessary and unsupported by precedent. He contended that previous cases cited by the majority did not establish such a rule, but rather required an examination of whether prejudice resulted from denial of counsel. Furthermore, he disagreed with the notion that prejudice should be presumed in these situations, asserting instead that it must be proven. Additionally, he criticized the court's reliance on Holloway v Arkansas as misplaced since this case dealt with conflict of interest which is different from absence or denial of counsel altogether.