The U.S. Supreme Court on Monday struggled with just how bad a lawyer must be to warrant stopping the clock on the time for filing a prisoner’s federal habeas petition.

In Holland v. Florida, the justices confronted two issues: whether the one-year deadline for filing habeas petitions under the Antiterrorism and Effective Death Penalty Act can be tolled for equitable reasons, and whether a lawyer’s gross negligence is one of those reasons for halting the clock.