Attack on the Holts

The Attack on the Holts was an attempt of Azazel to feed demon blood to Rosie Holt.

Background
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.

Battle
Later that night, Sam and Dean noticed the omens that accompanied Azazel. They rushed inside the Holts household, with Sam wielding the Colt. Sam went straight into the nursery room, where the demon was already starting to kill Monica Holt by pinning her to the ceiling. Sam then fired at the demon, but Azazel vanished before he could be shot.

Aftermath
Sam and Dean saved the Holts family and prevented Rosie from being fed demon blood. However, they lost one bullet of the Colt and failed to kill Azazel. They were also separated from their father John.