This special issue of Organization treats cooperatives as alternative forms of business and organization, focusing on worker-owned-and-governed forms. In reviewing extant research and considering the seven articles in this special issue, we treat five main challenges that workers’ cooperatives face: (1) the organizational resources, structures, and dynamics allowing for social as well as economic resilience for worker cooperatives; (2) the complex types and roles of leadership in worker cooperatives and related organizational forms; (3) the capacity of and obstacles to the reinvention of democracy within cooperatives; (4) the relationships between cooperatives and organized labor, the state, the community, and the larger financial system; and (5) the pursuit of cooperative values and policies within international market and environmental contexts. The examination of these challenges in relation to the worker cooperatives specifically can inform new projects in employee ownership and governance as well as perhaps assist with democratic organizational transformations in other firms and sectors.