This chapter discusses Defoe’s involvement with the law and the penal system, focusing on his brushes with the censorship laws, resulting in his experience of prison, as well as his business failures and imprisonment for debt. The second half treats Defoe’s representation of the law and prison in his fiction. The chapter outlines the British judicial and penal system at the end of the seventeenth and the beginning of the eighteenth century, underlining the differences from today’s situation in the UK. It also discusses Defoe’s representation of Newgate in Moll Flanders in its historical and literary contexts. The latter is especially linked to Defoe’s creative inflection of the genre of the criminal (auto)biography with its moral and religious overtones. The chapter also provides a brief summary of the contemporary sedition and libel laws and how Defoe fell foul of these.