In this chapter, we advance an understanding of entrepreneurial resourcefulness in relation to context by focusing on challenging and sometimes outright hostile environments and the way they shape, and are shaped by, entrepreneurial resourcefulness. Drawing on selective evidence from several projects in post-socialist countries in both Central and Eastern Europe and Central Asia and other published research covering these countries, we argue for contextualized conceptualizations of resourcefulness. More specifically we emphasize that temporal, historical, socio-spatial and institutional contexts are antecedents and boundaries for entrepreneurial behaviour, whilst at the same time allowing for human agency. This is visible in individuals’ actions to negotiate, re-enact and cross these boundaries; and as a result, intentionally or inadvertently contributing to changing contexts. We suggest that resourcefulness is a dynamic concept encompassing multiple practices, which change over time, and it results from a close interplay of multiple contexts with entrepreneurial behaviour. We also propose that from a theoretical point of view, resourcefulness not only needs to be contextualized, but it also needs to be explored together with its contextual outcomes – the value it creates and adds at different levels of society.