Captain Alexander Maconochie was the most innovative and controversial figure in the history of British convict transportation. This chapter examines Maconochie’s term as commandant of Norfolk Island, from 1840 to 1844 whose contested history in many ways lies at the heart of the convict transportation debate. It considers the religious sources for the ‘social system’ that Maconochie first attempted to implement on Norfolk Island, the most original and daring experiment in the long history of British convict transportation. It interrogates Maconochie’s radical disagreement with Colonel Arthur and other defenders of Evangelical modes of penal governance in Van Diemen's Land and why the mark system secured the support of other clerical writers on penal reform. With the abrupt cancellation of Maconochie’s experiment, Norfolk Island became an essential stage in Lord Stanley’s probation system. This chapter will go on to assess the role of clerical commentators on the later, tragic history of Norfolk Island and the role they played in its closure.