One of the most central themes in The Scarlet Letter is the clash between the individual and society. The book's opening look at the prison house is a primary example. Although the Puritans had hoped to establish a utopian society in the New World, one where everyone would be united under a shared ideology, their plan appears to have failed before it even began.

The prison was one of the first buildings created by the immigrants, suggesting their recognition that certain individuals would inevitably transgress the socially established rules. Unity was impossible. Obviously, Hester's transgression shows the conflict of individual passion with the group's regulations. Hester's daughter Pearl, whose entire existence, according to Dimmesdale, is evidence of the "freedom of a broken law," shows no reverence for law or society but lives in a completely self-defined world. In fact, Pearl's very existence is so contrary to Puritan beliefs that the author, Nathaniel Hawthorne, ships her off to Europe at the novel's end, showing her inability to live happily within this society's narrow boundaries.

Building on this problem of how individuals should interact with social rules, Hawthorne introduces a cluster of similar questions. For example, who should have the right to judge individuals' behavior? Do the old, desiccated magistrates have the right to judge Hester's passionate action? Does Chillingworth have the right to judge and to administer private vengeance upon Dimmesdale?