Goldfein flew combat missions during the Gulf War, and later deployed to the Vicenza Combined Air Operations Center for Operation Deliberate Force. As commander of the 555th Fighter Squadron, he led his squadron flying an F-16 fighter in Operation Allied Force. During that operation, on 2 May 1999, Goldfein's F-16 was shot down over western Serbia by a S-125 surface-to-air missile fired by the 3rd Battery of the 250th Air Defense Missile Brigade of the Yugoslav Air Force. Goldfein successfully ejected, and was subsequently rescued by NATO helicopters.