The Trump administration has issued a two-week deadline for Cuba to release political prisoners as part of ongoing talks aimed at reshaping economic and political relations between Washington and Havana, according to a source familiar with the discussions.

The demand was delivered during an April 10 meeting in Cuba involving a senior U.S. delegation, marking the first time a U.S. government plane has landed on the island since 2016. Officials said the move is part of a broader push to secure concessions from the Cuban government while addressing longstanding concerns over human rights and economic policy.

Among those identified for possible release are dissident figures Luis Manuel Otero Alcántara and Maykel Osorbo, both associated with the San Isidro movement and sentenced in 2022.

A State Department spokesperson said the administration remains committed to securing the release of all political prisoners and pointed to recent remarks by Donald Trump signaling that a “new dawn for Cuba” could be possible if reforms are implemented.

U.S. officials also warned Cuban leaders that the island’s economy is deteriorating and could worsen without structural changes. The administration is seeking expanded political freedoms, compensation for confiscated American-owned property, and policies that would open the economy to greater foreign investment.

As part of modernization efforts, the proposal includes introducing high-speed internet service through Starlink to improve connectivity on the island.

The discussions reportedly included outreach beyond official channels, including contact with individuals connected to former Cuban leader Raúl Castro.

Tensions between the two countries have increased in recent weeks as Washington has tightened sanctions and restricted oil shipments to Cuba. While the administration has indicated it prefers a diplomatic resolution, officials have also suggested additional measures remain under consideration if Havana does not comply.

Negotiations are ongoing, with the coming weeks expected to be critical in determining whether the two sides can reach an agreement on the proposed reforms and prisoner releases.