**US military contingency planning for Cuba has advanced amid the Trump administration’s intensified sanctions and embargo measures, though President Trump has repeatedly stated that a deal remains the preferred path and that military force is unlikely to be needed.** In September 2026, reports detailed ongoing SOUTHCOM support assessments by the Army Reserve and earlier examinations of options such as air assaults involving the 101st Airborne Division, alongside reconnaissance and heightened readiness. These steps coincide with fuel shipment seizures, secondary sanctions targeting Cuban entities and foreign partners, indictments of regime figures, and demands for political change. Cuba has maintained limited communication channels while bolstering defenses and rejecting negotiations on its system of government. Trader assessments reflect the gap between sustained pressure and the absence of deployment orders or imminent triggers, alongside the administration’s public emphasis on economic leverage and negotiated outcomes over direct intervention.