The growing emphasis on rural small and medium size entrepreneurship for economic development, especially in the context of poverty alleviation in developing countries has thrown up some major challenges for the commercial ventures led by women in global perspective. The position of women, even in the developing world, has been far from uniform or nonlinear in this emerging global scenario. Against this backdrop and through several exemplary cases around the world, this paper intends to highlight that women entrepreneurs have made some gains and its emerging role in the rural African setup given the imminent global economic crisis. The market for e-business and e-commerce is, at least potentially, has strengthened their ability to more effectively compete even in the domestic market. A number of such interventions in the area of IT based commercial enterprises for women have been undertaken all over the world. This paper, therefore, underlines the strategic challenges and opportunities from a gender focus to analyze the prospects of rural small and medium entrepreneurship for women through an analytical research on women’s IT-based commercial enterprises and present a matrix of issues before the women entrepreneurs.