This chapter, reflecting the changes in critical understanding of Oliver Twist in recent decades, addresses two themes: Oliver Twist’s urban aesthetic, and the topos of the homeless child. Oliver’s London has been read as a place of squalor, alienation, and danger, as opposed to a countryside idyll. Within this binary, the child is understood as an emblem of innocence, immune to the corrupting influence of the urban setting. Establishing a more benign Dickensian urban ecology, the chapter discusses the urban experience as a precondition of Bildung (education, formation), allowing for greater agency and individual growth. The rural, albeit peaceful, is regressive, monologic, and morbid. Such a reading allows for re-examination of Oliver’s freedom of choice and challenges the contention that he is but a static, helpless pawn in the hands of others. Oliver’s moments of weakness and loss in the urban labyrinth are opportunities for empowerment that enable him to invent himself anew.