Contextualisation research in entrepreneurship is on the rise. Scholars generally view it positively, as contextualisation allows for a better understanding of the bigger picture, whilst also concerns are voiced. However, contextualisation may lead to an overly fragmented field and its possible disintegration. This calls for ‘the emergence of sensible approaches to contextualisation that provide guidance in balancing its benefits and costs’ as reported by Welter et al. (Small Business Economics 52(2):319–330, 2019) which is the challenge we address in this Special Issue. More specifically, we argue that an investigation of the construction and enactment of contexts provides a path to better understand the identified tension. The aim of this Special Issue ties in with increasing calls in the entrepreneurship literature for going beyond agent centric views towards accounts that theorise the interconnections between agency and structure. Taken together, the articles in this special issue contribute to (1) a stronger grounding for entrepreneurship theories and concepts; (2) a more balanced conceptualisation of both agency and context; (3) a shift from the ‘standard model’ of entrepreneurship; and (4) context sensitive entrepreneurship methodologies and approaches. We end with identifying further research avenues.