Digital entrepreneurship is a catalyst for economic growth and innovation in developing countries, yet gender inequality remains a significant barrier. This study explores the intersection of gender and digital entrepreneurship through Gender Role Theory, focusing on how societal norms, financial constraints, and institutional shortcomings hinder women’s participation. Using case studies from Kenya, India, Bangladesh, Rwanda, and Indonesia, the research evaluates the effectiveness of empowerment programs and policy initiatives aimed at fostering gender-inclusive digital ecosystems. Key findings reveal that restrictive gender norms, financial exclusion, and digital literacy gaps significantly impede women’s entrepreneurial efforts. Limited access to mentorship, business networks, and funding further deepens disparities. However, targeted initiatives—such as Akirachix in Kenya, India’s Digital Literacy Mission, and Bangladesh’s Grameen Bank Model—demonstrate the potential of tailored interventions to improve digital skills, financial inclusion, and professional support. Rwanda’s gender-sensitive legal reforms and Indonesia’s digital literacy programs underscore the importance of policy innovation. Despite progress, systemic biases and entrenched cultural expectations continue to limit scalability and impact, especially for rural and marginalized women. Moreover, many programs overlook intersectional barriers, leaving vulnerable groups without adequate support. The study highlights the need for context-specific, multi-stakeholder strategies that combine policy reform, community engagement, and cultural transformation. To build an inclusive digital entrepreneurship landscape, governments, private sectors, and global actors must expand access to gender-sensitive education, financial resources, and mentorship. By addressing institutional bias and leveraging digital innovation, developing countries can unlock the full potential of women entrepreneurs, driving sustainable growth, innovation, and social change.