S3, E16: Dean's deal with the crossroads demon is up in 30 hours and Dean, Sam and Bobby (recurring guest star Jim Beaver) search for Lilith, who holds the contract. They discover her location and Sam summons Ruby (recurring guest star Katie Cassidy) for help, despite Dean's protests. Ruby warns them that they aren't yet ready to fight Lilith, but they steal her knife and depart for New Harmony, Indiana. In a battle to the death, Sam, Dean and Bobby take on Lilith and all her demons in a last ditch effort to save Dean's life.