The Trump administration's maximum-pressure campaign on Cuba, including an oil blockade, expanded sanctions on foreign enablers, and explicit calls for regime change, has kept bilateral engagement limited to lower-level official contacts. Reports from March 2026 indicated U.S. negotiators told Cuban counterparts that President Miguel Díaz-Canel must step down for meaningful progress, a demand Havana rejected outright. Díaz-Canel has publicly confirmed early-phase talks aimed at addressing bilateral differences but emphasized no preconditions involving leadership changes. As of late May, President Trump signaled possible future discussions without referencing a direct call, while continuing to criticize the Cuban government. These dynamics, combined with the short window to June 30, underpin the 91% implied probability against a Trump-Díaz-Canel conversation occurring.