Between 1787 and 1868 the British government dispatched over 160,000 convicts to its penal colonies in New South Wales, Van Diemen's Land and Western Australia. A question that has interested historians of crime about this mass transportation of convicts has been its impact on colonial offending rates. Several studies have explored the rate of reconviction amongst offenders shipped to Australia's penal colonies. This chapter presents the detailed analysis of life cycle offending amongst a cohort of male convicts shipped to Van Diemen's Land. Transportation to Van Diemen's Land can be split into two phases: assignment, which for men lasted until 1839, and the probation system which replaced it. If transportation really did help to make Tasmania a relatively crime-free colony as has been argued by some then it is probation, rather than assignment, that should take the credit. While transportation to Tasmania was widely condemned in the nineteenth century, recent reassessments have been more positive.