|Air Attacks on Puerto Rico|
|Part of Battle of the Atlantic|
Clockwise from top: Cuban Air Force MiG-21s on a strafing run, damaged ships as a result of a Cuban air attack on Roosevelt Roads Naval Station, U.S. Navy F-4 Phantoms about to engage Cuban fighter jets.
Upon Cuba's entry into the war, the country invaded the Bahamas, Haiti, the Dominican Republic, and the British Overseas Territory of the Turks and Caicos Islands. The self-governing U.S. territory of Puerto Rico was not spared from these attacks, although an invasion never materialized due to Cuba's distance from the island. The primary target of the Cuban Revolutionary Air Force was the U.S. Navy's Roosevelt Roads Naval Station located on the northeastern tip of the island near the town of Ceiba, along with other U.S. Navy facilities in Vieques Island. Attacking it would have been a strategic victory for the Cubans since it would cripple any American naval presence in the Caribbean.
The first air attacks occurred upon the fall of the Bahamas and the TCI. Cuban fighter jets launched strikes on military positions in the island. San Juan and Ponce were also attacked, killing roughly 700 civilians in the span from November 1989 to February 1990. The Puerto Rico National Guard was mobilized to defend the beaches around Puerto Rico as the United States Air Force, alongside the Puerto Rico Air National Guard as well as the U.S. Navy fighter jets scrambled to shoot down the Cubans. Anti-aircraft batteries opened fire on Cuban fighter jets above the skies. The air attacks damaged the Roosevelt Roads Naval Station, which managed to sink or cripple at least four frigates, one supply ship, ten patrol craft, six minesweepers, three landing ships, and one destroyer which capsized. Despite the relentless air attacks, technological superiority was on the side of the Americans as the Cuban MiG-21s were no match for the U.S. F-14, F-15, F-16, and F-18s. The tide turned when U.S. President George H.W. Bush ordered the nationalization of the Puerto Rico National Guard and the Virgin Island National Guard, effectively banding them together. This made coordination against enemy fighter jets even easier. By February 1990, Cuba ceased their air attacks on Puerto Rico after losing roughly the majority of their air force.
Roosevelt Roads Naval Station suffered moderate damages during the air attacks. Several ships were destroyed, alongside some naval aircraft on the ground. The capital of San Juan and Ponce also suffered structural damages and over 700 civilian casualties from the air raids.
In the aftermath, Puerto Rico became a main allied naval base, especially for ships coming from the United Kingdom, France, and the Netherlands in preparation for the liberation of the Caribbean islands that were continued to be occupied by Cuba, as well for the Allied Invasion of Cuba itself, codenamed Operation Doorbell.