In 1944, Gilbert did a six-month tour of Alaska with the United Service Organization (USO) with Thelma White, an actress and comedian. The group performed for men in hospitals and camps at various airbases where the band still experienced some gender-based discrimination. One night, high-ranking officers cancelled a hospital ship show so that the women in the band could "mingle at a party instead." The band, however, was able to leave the party and make it in time to perform, which was what they had come to do.