The Trump administration’s maximum-pressure campaign—through expanded sanctions, an oil embargo, and targeted restrictions—has driven heightened trader focus on potential US military action against Cuba. Pentagon contingency planning, including Army Reserve assessments for SOUTHCOM support units and prior reconnaissance around the island, surfaced in late September reports, though no deployment orders have been issued. President Trump has repeatedly stated a preference for a negotiated deal, describing Cuba as a failing state open to US influence without military involvement. Cuban officials maintain communication channels but reject formal talks, while publicly boosting defensive preparations against aggression. These dynamics, amid Cuba’s severe energy and economic strains, shape assessments of escalation risks through year-end.