Women's entrepreneurship through microfinance programs has been celebrated as a model for reducing poverty and empowering women. Yet, evidence of the incidence of women's entrepreneurship has been disappointing, leading to much critique and controversy. This article presents case narratives of women enrolled in microfinance programs in rural India who took the leap onto entrepreneurship and used microcredit loans to expand or start their small-scale livelihoods enterprises. These narratives illustrate the particular economic and social conditions that are found in cases where women have transitioned from being dependent, gender-compliant housewives to sole-earners or main breadwinners. Marital failure, functional absence or retreat of husband, economic distress, living in a nuclear household, and absence of an adult son are consistently evident in all cases of women's entrepreneurship. This qualitative analysis helps us understand why women's entrepreneurship is not more widespread despite the availability of microcredit loans.