The ‘horrors of transportation’ originated with William Bernard Ullathorne, Catholic vicar general of New South Wales. It was given greater prominence through his testimony to the Molesworth SC on Transportation. The Molesworth SC provided a vehicle by which Gothic elaborations of convict demoralization were woven together with traditional Catholic teaching on the purgatorial suffering of the damned and conservative Protestant fears of Catholic incursion on the moral realm. In the penal colony, fears of a calamitous rise in crime were stoked by Judge Burton in the New South Wales Supreme Court. Burton and Ullathorne would go on to engage in a sparring match over the relative number and moral status of Catholics in the colony and who should receive funding to run schools, churches and provide religious instruction to convicts. Convicts, including political prisoners, wrote their own accounts of the 'horrors of transportation', which heightened anxieties about the moral status of convicts and the penal colonies. This chapter provides a brief outline of Catholic teaching on penal reform and why this matters to the sectarian dispute which broke out between Ulltathorne and Burton and the anti-transportation debate.