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The Trump administration continues to ratchet up economic pressure on Cuba and is inching closer to military action as it looks to weaken or even topple the regime there.

The Asian Katra, a Panama-flagged cargo ship, arrives in Havana Bay carrying humanitarian aid, in Havana, on May 18, 2026. | Adalberto Roque/AFP via Getty Images

President Donald Trump has struggled to lure businesses back into Venezuela after deposing its authoritarian leader in January. Cuba could be an even harder sell.

The Trump administration continues to ratchet up economic pressure on Cuban President Miguel Díaz-Canel with sanctions and an energy blockade and is inching closer to military action as it looks to weaken or even topple the regime there.