The idea of man’s ‘mastery over nature’ is ubiquitous in western philosophy and in western thinking. Technology has been widely used in support of this end. Given the growing interaction design opportunities for personal digital technologies in supporting outdoor and recreational nature activities such as mountaineering, it is timely to unpack the role that technology can play in such activities. In doing so, it is important to consider the intrinsic and extrinsic motivations at play for the individual and the accepted social norms or ‘rules’ that are associated with the activity through its community and passed on through its community of practice. Technologies that may be considered as a form of ‘cheating’ when first introduced (such as handheld GPS) can later become accepted through common practice, although the rules are often nuanced. For example, it is widely regarded that GPS should not replace the skill of map reading and navigation. In this chapter, we consider different forms of mastery over nature that technology can support and reflect on the design sensitivities that these provide.