In 2003 the United States Commission for Assistance to a Free Cuba was formed to "explore ways the U.S. can help hasten and ease a democratic transition in Cuba". Since 2005 the commission has been chaired by Condoleeza Rice and seeks to integrate the administration's Cuba policies with all the agencies of the federal government. In response Fidel Castro called the Commission a "group of ****-eaters who do not deserve the world's respect,". Castro also referred to Rice as a "mad" woman and US Chief of Mission in Havana Michael E. Parmly as a "little gangster" and a "bully". Castro has insisted that, in spite of the formation of the Commission, Cuba is itself "in transition: to socialism [and] to communism" and that it is "ridiculous for the U.S. to threaten Cuba now".

The Bush administration appointed Caleb McCarry "transition coordinator" for Cuba, providing a budget of $59 million, with the task of overthrowing the Cuban government after Castro's death. Official Cuban news service Granma alleges that these transition plans were created at the behest of the Miami Mafia, and that McCarry is responsible for engineering the overthrow of the Aristide government in Haiti. On the establishment of McCarry as post-Castro transition coordinator, Organization of American States Secretary General José Miguel Insulza said, "There's no transition and it's not your country."