**Recent U.S. policy toward Cuba has centered on sustained economic sanctions, expanded intelligence operations, and targeted pressure for political transition rather than direct military intervention.** Under the Trump administration, officials including Secretary of State Marco Rubio have imposed repeated sanctions on Cuban state entities, mining firms, and influence networks while exploring potential transitional figures. Earlier 2026 statements from President Trump referenced possible action similar to the Venezuela operation, and Pentagon planning examined limited options, yet concrete steps have remained in the coercive-diplomacy lane. Bilateral talks resumed in August 2026 with Cuban leaders expressing willingness to address differences through dialogue on equal terms. Cuba continues facing severe fuel shortages, power outages, and economic strain following the cutoff of Venezuelan oil supplies, but U.S. actions have emphasized blocking external support and closing “escape valves” over kinetic escalation. With the calendar now approaching September and no mobilization or ultimatum signaling imminent invasion, traders assign the 93.5% probability to “No,” reflecting the administration’s apparent preference for gradual regime pressure extending potentially into 2029.