In Cuba and the United States, Protestant institutions exist that are both reflective and nonreflective about their culture’s influence on belief and practice. The case of Cuba sheds light on how Christian churches and voluntary associations operate in an authoritarian regime. Despite the tension and enmity that have typified Cuba’s geopolitical relationship with the United States since the colonial days, cross-cultural Christian philanthropic partnerships exist. The “doble carácter” (double character) of Cuban Protestant churches has grown out of both collaboration with, and resistance to U.S.-style evangelicalism (Arce Valentín 2016). Adaptations of liberation theology, adopted among Cuban Christians, provide an influential counterweight to the mighty Western theological and philanthropic tradition (González 2012). The nature of this engagement influences Cuban civil society, the survival of the Cuban regime, and provides an extreme case for cross-cultural philanthropy worldwide. This socio-historical account utilizes the data collected from personal interviews with Cuban Protestant leaders, primary sources found in the library at the San Cristobal Presbyterian Seminary and Cuban theological journals, and a qualitative analysis of literature on Cuba, Protestants, missions, philanthropy, nongovernment organizations (NGOs) and civil society. View Full-Text