S3, E12: Sam and Dean break into Bela's (recurring guest star Lauren Cohan) apartment in order to get the Colt back, but she has tipped off Agent Henricksen (recurring guest star C. Malik Whitfield) to their whereabouts, and the brothers are arrested. Sam and Dean are locked in a cell in Colorado when a demon breaks in. It kills some of the sheriff's men and possesses Henricksen. After Sam and Dean vanquish the demon, Henricksen realizes the boys were telling the truth and prepares to release them. Ruby (recurring guest star Katie Cassidy) shows up to warn Sam and Dean that a band of demons is surrounding the jailhouse; with the demons is a powerful new leader who wants Sam dead.