In the spring of 2011 when citizens in Arab countries rose up against their regimes, it appeared that the “third wave” of democratization had begun in the Middle East and the Maghreb, and that countries would embark on successful democratic transitions. Issues such as the gendered nature of the uprisings, how gender relations and women’s mobilizations have shaped trajectories, as well as how women and their rights have been affected, have been under-researched. In this article, I put the spotlight on North Africa—Algeria, Egypt, Libya, Morocco, and Tunisia—which saw different protest dynamics and political outcomes subsequently. Drawing from mainstream literature on determinants of democratization and feminist literature on women and democratic transitions, I examine how women’s preexisting legal status and social positions, as well as the broad structural, institutional, and cultural contexts, shaped the course and immediate outcomes of the Arab Spring in the countries examined. I argue that those countries that saw advances in women’s participation and rights prior to the Arab Spring are the ones most likely to transition successfully to democracy, and indeed, to establish a more women-friendly democracy; and that women’s growing political leadership will influence the quality of ongoing democratizations in the Maghreb countries of Algeria, Morocco, and Tunisia.