This chapter argues that sites of punitive relocation were important locations for colonial encounters, exploration, and knowledge formation. Their relatively open character meant that many convicts lived and settled in already dynamic societies in which Indigenous peoples, settlers, labour migrants, and/ or enslaved persons lived. Thus, they constituted ideal vantage points for the observation of Indigenous peoples, and for commodity exchange. Central points here are that Indigenous people greatly assisted the process of penal colonization that at the same time dispossessed and devastated them, and they encountered and resisted the people who came to live in sites of penal relocation in a variety of ways. From a history of science perspective, it is also significant that the separate penal colonies established in nations and empires from the late eighteenth century onwards were often located in relatively pristine natural spaces. Penal administrators and visiting naturalists, botanists, geologists, and zoologists exploited these natural resources in their scientific research – often assisted by convicts and Indigenous peoples. Convicts and colonized populations played a vital role in Europe’s so-called voyages of discovery, with scientists drawing on their superior local knowledge and practical support.