US military contingency planning for Cuba has advanced in recent months amid the Trump administration’s maximum-pressure campaign of sanctions, secondary restrictions on fuel shipments, and accusations that Havana maintains ties with Russia, China, and Iran. Reports in late September detailed Army Reserve assessments of logistics, medical, engineering, and military-police units that could support U.S. Southern Command within 90–120 days, though no deployment orders have been issued and senior officials have described the activity as ongoing contingency work rather than active preparation for invasion. President Trump has repeatedly stated that a deal is expected and military action is unnecessary, while Cuban diplomats have confirmed only informal communication channels exist and have publicly emphasized defensive preparations. These developments frame trader assessments of near-term military action around the balance between sustained economic coercion and the absence of confirmed operational orders.