Azazel continued to enter more homes with six-month old children. The Winchesters tracked the demon down to Salvation, Iowa, where the Holts family lived. Finally having acquired the Colt, a weapon that could kill a demon, the Winchesters decided to kill Azazel before he had the chance to complete his goal on the Holts family. However, Azazel's daughter began to kill John's friends one by one in an effort to discourage the Winchesters from using the Colt against demons. She threatened to kill more of John's friends until John gives up the Colt. John decided to leave the Colt to his sons while he would meet up with the demon to surrender a replica of the Colt. After much argument and deliberation, John went on with the plan and tasked Sam and Dean to kill the demon.
John arrived at their rendezvous earlier than agreed to by both parties, in order to bless the water running in the pipes of the compound. Once the demons arrived, John surrendered the replica. Meg passed the Colt to her brother Tom, who casually shot his sister, demonstrating that the gun John surrendered was not the Colt. John fled the scene immediately but the demons gave chase. They were temporarily blocked by a stream of holy water that John blessed earlier. Before John could escape however, he found out his truck was damaged. Eventually, he was caught by the demons.
John was kept as a prisoner of the demons, while Meg would continue her hunt for the Colt, leading her to Sam and Dean.