Given that women in patriarchal societies face structural barriers hindering their participation in entrepreneurship, it is imperative to explore women’s engagement in entrepreneurship, navigating these barriers. The proliferation of digital technologies marks transformative changes in the entrepreneurial landscape and offers critical crossroads for women to engage in entrepreneurial businesses. Thus, recently scholars have started investigating the emancipatory potential of female digital entrepreneurship, which has received limited academic attention thus far. Bridging the gaps in extant literature, the primary focus of this PhD study is an exploration of the emergence of digital entrepreneurship as a liberating pathway for women in developing economies in the South Asian region. To attain a holistic understanding, first, the factors that drive women to disrupt the status quo and participate in digital entrepreneurship were investigated. To identify these factors, Individual Differences Theory of Gender and IT (IDTGIT) was extended to the arena of female digital entrepreneurship. Furthermore, the research drew on the theoretical lens of intersectionality to investigate how gender intersects with other social ascriptions that may affect women’s pathways to emancipation. The Digital Affordances concept was also drawn upon to explain how women use digital technologies. Second, the study focused on critically exploring changes in the broader social order activated through women’s engagement in digital entrepreneurship. The study was conducted utilising a sequential mixed methods approach. Initially five informal interviews were conducted with key stakeholders to attain a broader understanding about how digital entrepreneurship takes place at the grassroot level. Then using a survey of 159 female digital entrepreneurs in Sri Lanka, the hypothesized relationships were empirically tested. Finally, in-depth interviews were conducted with 25 female digital entrepreneurs to further explore the phenomenon. The integrated findings showcase emancipation as a two-way interaction where contextual factors shape women’s participation in digital entrepreneurship and how their endeavours result in change in the broader socio-cultural context. It was found that women’s engagement in digital entrepreneurship is shaped by environmental influences; individual influences; and personal demographics. Furthermore, women who start and run businesses by utilising digital technologies were found to activate broader social change which result in legitimisation of female digital entrepreneurship. Even though there were some instances where women’s engagement in digital entrepreneurship led to reinforcing the patriarchal norms, the positive changes remain significant. Overall, this research contributes a comprehensive model on digital entrepreneurship as emancipation which can be utilised as a framework for future research.