On 14 August 1962, the squadron performed a non-stop air refuelled deployment to Naval Station Roosevelt Roads, Puerto Rico and Naval Station Guantanamo Bay, Cuba. Of the 22 aircraft in the squadron 4 were initially stationed at Gitmo as armed Hot Pad Alert aircraft. The rest of the reinforced squadron (parts of Marine Air Base Squadron 32 and Headquarters and Maintenance Squadron 32 were attached) at Roosevelt Roads engaged in advanced tactics, gunnery and missile training while living in a tent city that served as a deployment test site. The squadron was already in position when the Cuban Missile Crisis erupted in October 1962 and the aircraft numbers at Gitmo were reinforced should the need have arisen to strike targets in Cuba. During the crisis, VMF-333 was joined by Marine Attack Squadron 331 and assumed tactical command over the Puerto Rico Air National Guard's F-86 aircraft as a combined Puerto Rico Air Defense Command. Trip Tree returned to MCAS Beaufort in December of that year after the crisis was resolved.