In Cuba in the 1990s, the collapse of USSR had important repercussions on the economy, and the population survived only in extreme poverty. The seriousness of the crisis made it necessary to redefine the ideology of the political regime, while the Catholic Church assumed an important social role thanks to international Catholic aid. It is in this context that the Castro State and the Catholic Church entered into a new relationship, one which made possible a papal visit in January 1998. Despite the conciliatory tone of the official discourse of both institutions, however, tensions still existed between them. The State encouraged tolerance towards religion, even inside the Communist Party, but made sure to promote religious diversity in order to reduce the Church’s power. The Church was still perceived as a pole of ideological opposition to the regime. The aim of this article is to recount the strategies of State and Church as they approached each other with mistrust during the period 1990 to 2005. It also attempts to understand how the population of Havana reacted to both institutions in terms of their discourses and social roles.