This study explores the responses of women digital entrepreneurs to overlapping social and digital contexts whilst building legitimacy. Using qualitative empirical analysis of 21 in-depth interviews with women digital entrepreneurs in Nigeria, the findings reveal the complex process of legitimacy building. Far from reducing gendered structural barriers, the digital context overlaps with the social context. This overlap is characterised by paradoxical tensions and constraints. Women digital entrepreneurs respond to these by adopting different and multi-faceted legitimation practices, enacting what we propose to call eclectic legitimation work. This paper thus makes two contributions to the understanding of women digital entrepreneurship. First, building on advances from the cyberfeminist perspective, the paper draws on Paradox Theory to reframe women digital entrepreneurship as inherently paradoxical in the way it is experienced and navigated by women in their everyday lives as digital entrepreneurs in overlapping contexts. Second, the paper engages with the under-explored aspect of legitimacy building in women digital entrepreneurship. It reveals the different facets of legitimation work and the different sets of responses adopted by women digital entrepreneurs. This underpins our conceptualisation of the eclectic legitimation work that these women entrepreneurs undertake to navigate these tensions and build legitimacy.