In 2005, the Institute for Democracy in Eastern Europe renewed its Democracy for Cuba Program with a set of multifaceted activities — including delegations, exchanges, democracy publications, and the establishment of an Eastern European Advisory Council for Democracy in Cuba, among others. The program is ongoing. The aim of the program is to draw upon the experience of Central and East Europeans in dealing with communist regimes and to involve them in concrete efforts to help break through the Castro regime's information blockade of the outside world and to support the Cuban democracy movement  Through these ongoing activities, Central and East Europeans are also sharing their experiences about their countries’ transitions from communism and offering assistance in the struggle of Cuban dissidents for a peaceful transition from communism to democracy.

Cuba and Eastern Europe have been intertwined ever since Fidel and Raul Castro imposed a communist regime on the island fifty years ago. Using the help of the Soviet Union and its allies, the Castros learned how to centralize the economy, bureaucratize the government, and impose the state's control over the lives of citizens. Most significantly, Cuba adopted the entire repressive ideology and apparatus of the Soviet Union. In turn Cuba's police and army served at the orders of the Soviet Union both in organizinig subversion in Latin America or supporting revolutionary movements in Africa. During the long reign of the Castros, human rights have been totally suppressed and more than a million people have fled the regime's tyranny.

The fall of communism in Eastern Europe and the Soviet Union in 1989–91 offered some increased hopes for democratic change in Cuba as well. Instead,  the Castros have continued to adhere to the early form of Stalinism they adopted 50 years, including blanket repression, ideological mobilization, and total state domination. Today, the Cuban regime stands as the only member of the Soviet bloc that has not rejected or overthrown communism. It is only natural then that the democratic and civic activists who helped to overthrow communism in Eastern Europe feel a natural obligation to assist their Cuban counterparts and to offer some antidote to the secret police collaborators and agents who came to Cuba from their own countries.
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The need is clear. Just as in Eastern Europe, a small dissident movement has labored bravely to document the massive violations of human rights of the regime, to bring this information to the light of world opinion, and to help Cuban citizens overcome their fear to act — all in the face of terrible sacrifice. The Cuban dissident movement also adopted a strategy similar to Eastern European movemetns of promoting democracy through building civil society, a hope reflected in the united opposition manifest, "La Patria Es Para Todos (the Fatherland is for All)" issued in 1998. While there has not been a transformation similar to Eastern Europe, this strategy has seen a slow stirring of civil society over the last ten years in the form of free trade unions, agricultural cooperatives, lay groups, independent libraries, civic associations, human rights organizations, and community groups and activists.

IDEE began the first program to organize Eastern European support for the Cuban democracy movement at the request of Cuban opposition leaders in 1995. Over the next four years, IDEE organized trips of more than thirty opposition and dissident veterans from Eastern Europe to share their experiences with independent civic, trade union, cooperative, media, human rights, religious, and other communities. From 1996 to 2002, IDEE published a series of thirty pamphlets that provided Cuban activists with information and essays on East European opposition movements, the fall of communism, transitions to democracy in the region, and a series of essays called Cuba Democracy Pamphlets. IDEE worked with other organizations to establish a foundation of support among Eastern European public figures for promoting democratic change in Cuba.

IDEE’s renewed Democracy for Cuba program, which ran from 2005 to 2011 with support from the State Department's Bureau of Democracy, Human Rights, and Labor, continued these early dissident exchange and publishing initiatives, including the republishing of the original Democracy Pamphlets, publishing a new series of pamphlets (Democracia II and Democracia III) that focused on the experiences of communism, organizing opposition, and concrete areas of transition, like constitutional reform, human and minority rights, the rule of law, free market reforms, the role of trade unions, and other areas. Overall, during this period, IDEE: