The purpose of this paper is to report the preliminary findings of research in progress. The research area is debt accumulation in Van Diemen’s Land(VDL) between 1804 and 1833. In particular, the paper seeks to examine the relationship between inability to pay, the accumulation of debt and its consequences in VDL. The research spotlight is upon the work of the Lieutenant-Governor’s court between 1817 and 1823 and case studies of two cases in the VDL Supreme court between 1830 and 1833. The consequences of accumulated debts in VDL are investigated, in the search to understand why people did not pay debts in VDL between 1804 and 1833. The paper also reports the consequence of arrest at first instance for inability to pay debt and the response of the Hobart Town legal profession to this consequence: the development of Rule of Practice Number 11, adopted by His Honour Chief Justice Pedder on 3 May 1831. At this early stage in the research it is becoming clear that: (1) Getting into debt was a hazard of living in VDL between 1804 and 1833. (2) The legal consequences of getting into debt inflated the hardship of debt. (3) The legal profession of that time enjoyed ‘freedom’ to develop a legal response to ameliorate the specific ills suffered by residents of VDL.