New Zealand disproportionately captured the attention of US environmental historian Alfred Crosby in his book Ecological Imperialism. 1 He was not the first nor is he likely the last to see the country as an isolated island group of recent settlement that provides a fascinating case study of environmental transformation. This chapter in part continues this intervention though, in this instance, it is an insider viewpoint that is presented. Intersecting the theme of recent European settlement in New Zealand with the intellectual space opened up by the term ‘trading environments,’ conjures up at least three distinct and rich conceptual possibilities for the latter, concerned with ‘translation,’ ‘transformation,’ and ‘enterprise,’ which are elaborated on next. Thereafter these three separate but related imaginaries of ‘trading environments’ are explored in more detail through New Zealand examples but also by recourse to a discussion about ‘improvement,’ which was a powerful force in Western colonial settlement narratives. Albeit at somewhat different scales, these imaginaries consider, first, the rapid nineteenth century transformation of largely forested New Zealand into a farm landscape oriented, from the 1890s, toward supplying the British market with a limited range of meat and dairy produce; second, the simultaneous moves to reassess the land in terms of ‘natural value’ by protecting some limited areas for scenic purposes; and lastly, the relentless expansion of the settlement frontier that eventually produced regional episodes of land deterioration and disrupted the dominant settler discourse of progress and improvement. Collectively these three vignettes reveal how ‘trading environments’ offers a means of readdressing older debates about the course of rural land use in New Zealand, as well as posing new questions about how to understand key moments in the course of its European settlement and its aftermath in the late nineteenth and early twentieth centuries.