Soon after becoming a British colony in 1840, New Zealand began transporting convicts to Van Diemen's Land (VDL).This practice continued until transportation to VDL ceased in 1853. During this period, at least 110 convicts were sent across the Tasman Sea. Some were sentenced in the nascent colony's civil courts, and others as the result of courts martial. Almost half of those sentenced were British soldiers. This paper focuses on these serving and retired redcoats. It interrogates the circumstances that led to the arrests and trials of these men, focusing particularly on what this tells us about wider colonial society in New Zealand at the time, and about some of the soldiers' attitudes towards the New Zealand Wars. Attention will also be given to the backgrounds of some of the men, as well as to the circumstances of those who had retired, or deserted from, their regiments. The outcomes for this cohort of soldiers following their transportation to VDL will also be briefly canvassed.