The chapter explores the gap between the lived experience of Australia’s founding convict mothers and fathers and heritage site portrayals of penal transportation. It focuses particularly on Tasmania, formerly known as Van Diemen’s Land—which operated as a British penal colony in the years 1803–1853. We argue that a disproportionate number of convict heritage sites are located in former punishment stations. As such, much of the discourse about convict heritage interpretation has centered on the more brutal end of the system. While the use of punishment as a means of eliciting labor from convict bodies was an important part of convict experience, the measure of pain extracted was disproportionately borne by a few.