This market resolves YES if there is public confirmation from U.S. military officials, credible news sources, or official government statements that U.S. military aircraft conducted an overflight of Cuban airspace at any point during 2026. The overflight must be explicitly confirmed as occurring over Cuban territory (not international airspace). Resolution sources may include official Department of Defense statements, congressional testimony, major news outlets (Reuters, AP, BBC, etc.), or declassified government documents.

On January 3, 2026, the United States launched a military strike on Venezuela, codenamed Operation Absolute Resolve, which involved bombing infrastructure across northern Venezuela to suppress air defenses. Trump indicated that Cuban forces were involved in the operation, and the government of Cuba reported that 32 Cubans were killed in Venezuela, all members of armed forces and intelligence services.

Following the operation, the amphibious ships USS Iwo Jima and USS San Antonio were moved to the Atlantic, off the northern coast of Cuba. Secretary of State Marco Rubio, a longtime Cuba hawk, offered a warning for Havana, stating "If I lived in Havana, and I was in the government, I'd be concerned — at least a little bit".

Approximately 150 U.S. aircraft participated in the Venezuela operation, and Cuba's military is less equipped and less prepared compared to Venezuela's forces, with Cuba's military lacking modern air defense systems and being more geographically vulnerable. The proximity of U.S. naval assets to Cuba and heightened regional tensions following the Venezuela operation create a context where military overflights could occur, though no such overflight has been publicly confirmed as of January 2026.