Sikes and Oliver enter the house, and find Crackit and Barney, the younger Jewish man with the permanent head-cold. Crackit is relatively kind to Oliver, and asks him to drink a little liquor after his long journey. Oliver obliges, though he doesn't wish to do so. After eating a small amount, the men sleep, and tell Oliver to as well, until one in the morning, when they prepare to go out and commit the burglary.
Barney tends to appear in circumstances like this, where his presence is not strictly necessary, but when there are small tasks needing to be done. Although Barney in some ways serves as Fagin's foil, here he is his opposite: whereas Fagin is at the center of the gang's criminal plans, Barney seems only to do what he is told.
Crackit, Sikes, and Oliver make their way through the town of Sunbury in the middle of the night—it is so dark and foggy, they do not fear that they will be seen. They arrive at a farmhouse in the neighboring village of Chertsey. Sikes and Crackit help Oliver over the house's garden wall; Oliver realizes, at this point, just what the robbery will entail, and becomes extremely nervous, as he sees that Crackit and Sikes are prepared to use the firearms they have brought along.
Only now does Oliver realize the nature of the robbery. Again, Oliver's naiveté is obvious. Of course Oliver had a premonition that they trio was up to some sort of dangerous criminal behavior, but he does not know the exact form the robbery would take until the three reach Chertsey.
Sikes tells Oliver the plan: Oliver is going to be helped up to a very small window about five and a half-feet above the back-door frame; then Oliver will take a lantern with him, through the house, quietly so as not to startle those sleeping inside nor the dog there, and then to the front-door, which he will unlatch for the robbers. Sikes warns Oliver that he is within Sike's gun's range the entire way, in case Oliver wants to do something not in keeping with the plan.
Sikes is aware that Oliver is virtuous enough that he would be willing to risk his life rather than carry out the robbery. Nevertheless, the robbery is dependent on Oliver—he is the only one who can fit through the small window into the house. Thus Sikes must rely on Oliver.
Sikes helps Oliver into the house. Once inside, with a lantern, Oliver decides to run up the stairs to alert the family of the robbers, but just as he is doing this, two men appear at the top of the stairs above Oliver. Sikes tells Oliver to return to the window, but then a series of shot are fired by the men, and in the confusion, Sikes pulls Oliver back through the window and begins to run, with Crackit, away from the house. Sikes fires into the house but hits no one; as they are retreating, Sikes notices that Oliver has been hit by a bullet, and Oliver, frightened, faints in a dead swoon.
The low point in Oliver's young life. Oliver does not even get an opportunity to inform the family—he is shot by the overzealous Giles as he attempts to mount the stairs. Although Oliver almost dies in the ensuing night, this robbery marks a low point after which Oliver's luck only increases: he is taken in by the Maylie family, he finds out the nature of his birth-family, and he is adopted, ultimately, by Brownlow.