This chapter critically examines the persistent gender gap in entrepreneurial ecosystems, focusing on the structural, cultural, and educational barriers faced by women entrepreneurs in Portugal. Drawing on recent international literature and empirical data from 80 qualitative interviews with Portuguese women entrepreneurs, the study explores the multidimensional nature of women’s entrepreneurial trajectories, including social expectations, credibility deficits, and the interplay between personal and professional roles. The findings reveal that entrepreneurial motivation among women is often driven by necessity rather than opportunity, shaped by social constructs and historical inequalities. The study also highlights the latent influence of early informal learning, family environment, and socio-cultural norms on entrepreneurial behavior. By integrating global policy perspectives and updated recommendations from sources such as GEM, OECD, and UN Women, the chapter argues for the need to restructure entrepreneurial education through gender-responsive frameworks, digital inclusion, and mentoring-based methodologies. It concludes that fostering inclusive and diverse entrepreneurial ecosystems is both a social imperative and a strategy for sustainable innovation and economic development.