This research examines an individual experience of the colonial penal system during the years 1829 to 1869, that of recidivist convict, Robert Edward Knox, who was incarcerated for around thirty of his forty years in the New South Wales colony. The question of the historiographical and methodological value of the study of an individual life is at the centre of this research. By tracing Knox’s life and his experience of the colonial penal system over decades, the thesis is concerned to investigate the usefulness of the single case as a viable and productive approach in convict studies and seeks to contribute to greater understandings of convict experience and convict criminality.