When should a prisoner be held accountable for his attorney’s negligence or misconduct? Since the mid-1990’s, courts throughout the nation were deciding this question, after a growing tide of attorneys failed to meet the Antiterrorism and Effective Death Penalty Act’s one-year statute of limitations when filing federal habeas corpus petitions on behalf of their incarcerated clients. In Holland v. Florida, the Supreme Court decided once and for all when a prisoner would be given another chance to file his habeas corpus petition through the doctrine of equitable tolling when the only reason his petition was late was the fault of his attorney. This Comment explores the issues raised by the Holland decision. In doing so, this Comment analyzes the principles of agency law and professional responsibility—the foundations of the attorney-client relationship—and raises questions as to whether these principles are properly applied to incarcerated clients in the post-conviction context. This Comment ultimately concludes that while Holland was properly decided, the Court misapplied agency law to support its decision and did not go far enough in extending the protection of equitable tolling to all prisoners who have been turned away from the courts because they detrimentally relied on their defaulting attorneys.