Trump Administration Boosts U.S. Intelligence Operations in Cuba Amid Harder Line on Havana

The Trump administration has quietly expanded U.S. intelligence operations in Cuba as it increases pressure on the island’s communist government, according to a new report that suggests Washington is laying the groundwork for a broader strategy aimed at forcing political change in Havana.

POLITICO, citing two anonymous sources familiar with internal planning, reported Tuesday that U.S. intelligence agencies have increased their presence on the island in recent months. The officials described the move as part of a wider effort to give the administration additional options as diplomatic pressure on Cuba intensifies.

Neither the White House nor the Central Intelligence Agency publicly confirmed the report. The CIA declined to comment, while the Office of the Director of National Intelligence and the Defense Intelligence Agency did not respond to requests from POLITICO.

According to the report, one source said the United States has deployed additional intelligence personnel and assets to Cuba but declined to identify the agencies involved or discuss the scale of the operation, citing operational security concerns. A second source characterized the effort as an expansion of the CIA‘s footprint on the island but also declined to provide specific details.

The reported increase comes after years in which U.S. intelligence capabilities in Cuba were reduced following the mysterious health incidents known as Havana syndrome, which prompted Washington to withdraw numerous diplomats and intelligence personnel beginning in 2017. Although the cause of those incidents remains disputed, they significantly disrupted U.S. operations in Cuba for several years.

The renewed intelligence activity reflects the Trump administration’s increasingly confrontational approach toward Havana during the president’s second term. Since returning to office, Trump has restored Cuba’s designation as a State Sponsor of Terrorism, expanded sanctions and implemented measures designed to restrict the island’s access to foreign energy supplies.

Secretary of State Marco Rubio has played a central role in shaping that policy. The Florida Republican, whose parents emigrated from Cuba, has argued that the communist government bears responsibility for the country’s economic collapse and has repeatedly called for stronger measures to support democratic change.

According to POLITICO, one of the sources suggested the expanded intelligence presence could support a variety of future actions, including efforts to encourage defections within the Cuban government or military. The source also said increased intelligence collection could serve as preparation for a possible military operation, although no such action has been announced and the contours of any potential intervention remain unclear.

Military and intelligence experts note that expanding intelligence collection is a common step before major policy decisions, whether diplomatic, economic or military. Intelligence agencies routinely gather information on political stability, military capabilities and internal government dynamics to provide policymakers with a clearer picture of developing situations.

The report also places Cuba within the administration’s broader foreign policy agenda. Despite ongoing U.S. military commitments related to Iran, one source told POLITICO that Cuba remains a high priority, particularly for Rubio, suggesting the administration does not view the two issues as competing for attention.

The administration has already taken several high-profile actions involving Cuba this year. In May, CIA Director John Ratcliffe traveled to the island to deliver what POLITICO described as a warning urging Cuban leaders to pursue significant reforms. Days later, the Justice Department announced criminal charges against former Cuban President Raúl Castro over the 1996 shootdown of two Brothers to the Rescue aircraft, an incident that killed four people.

The report also noted that the administration believes intelligence operations contributed to the successful capture of Venezuelan leader Nicolás Maduro earlier this year, reinforcing the value officials place on expanding clandestine capabilities in the region.