The Trump administration has intensified economic pressure on Cuba through fuel shipment seizures, expanded sanctions on military-linked entities, and an oil embargo that has deepened the island’s energy and humanitarian crisis. US Southern Command contingency planning continues, including Army Reserve support assessments for potential operations, though President Trump has publicly stated that military action is unnecessary and predicted a bilateral deal. Cuba maintains informal communication channels with Washington but has rejected negotiations over its political system and reports increased defensive preparations. These factors, alongside the recent ouster of Venezuela’s Maduro that reduced Cuban oil supplies, drive trader assessments of escalation risks versus diplomatic or economic resolution paths in the coming months.