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The highest-level US-Cuba meeting in years came as negotiations on energy and political prisoners accelerated.

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US x Cuba diplomatic meeting by May 31?
CIA Director John Ratcliffe met Cuba’s interior minister in Havana on May 14, according to photographs released by the agency and reporting from El País. The meeting marked the highest-level face-to-face contact between the two governments in years, part of a broader surge in diplomatic activity.
The May 14 encounter followed a series of lower-level talks, including an April 10 meeting in which the US delivered a two-week deadline for Cuba to free political prisoners, USA Today reported, citing a State Department official. Cuba publicly denied that any ultimatums were issued, with senior diplomat Alejandro Garcia del Toro describing the exchange as respectful and professional.
Cuba confirmed in April that it had hosted a US delegation including assistant secretaries of state. The Cuban Foreign Ministry said Havana’s top priority in the negotiations is the end of the Trump administration’s tightened energy blockade. The island has been grappling with an energy crisis described as severe by international observers.
The negotiations have been opaque. El País reported that talks have been underway since March and have included multiple rounds, but neither government has provided a detailed public timeline. Cuba has not confirmed any further meetings scheduled for late May.
No official US or Cuban statement has announced a diplomatic meeting specifically by May 31. The next observable step remains any public confirmation from either government of continued or new talks.