CIA director John Ratcliffe on Thursday (May 14) delivered a message from President Donald Trump to top Cuban officials in Havana that the U.S. would "seriously engage" with the island´s government on economic and security issues "only if it makes fundamental changes," a CIA official told Reuters.

Still images were released on the CIA's X page on Thursday, showing Ratcliffe walking to a car in Havana, Cuba and at a meeting with Cuban officials.

Reuters was able to confirm the location of the image of Ratcliffe on the street with other personnel from buildings and road signage which matched archive and satellite imagery of the area. Reuters was not able to confirm images taken from indoors of a meeting that John Ratcliffe was attending. Date of images could not be verified however CIA official told Reuters that Ratcliffe met with Cuban delegates on Thursday (May 14).

Ratcliffe’s trip appeared to be only the second visit by a CIA director to Cuba since former leader Fidel Castro´s 1959 revolution, underscoring a rare moment of high-level contact between the two countries.

The CIA official, speaking on condition of anonymity, did not elaborate on the specific changes that Trump was demanding.

The U.S. has for decades demanded Cuba open its state-run economy, pay reparations for properties expropriated by the Castro government and hold "free and fair" elections.

Ratcliffe arrived amid spiraling tensions between Washington and Havana.

DESCRIPCIÓN DE IMÁGENES

HAVANA, CUBA (RELEASED MAY 14, 2026) (CIA via X - Must on-screen courtesy 'CIA via X') (MUTE)

1. STILL PHOTOGRAPH OF CIA DIRECTOR, JOHN RATCLIFFE (LEFT, FACING CAMERA) ON STREET

2. STILL PHOTOGRAPH OF RATCLIFFE (LEFT SIDE OF TABLE) STANDING AT A MEETING WITH CUBAN OFFICIALS

3. STILL PHOTOGRAPH OF RATCLIFFE (RIGHT SIDE OF TABLE, FACE UNBLURRED AT A MEETING WITH CUBAN OFFICIALS