Gilbert's band also began playing as The Victory Belles on a radio show geared toward servicemen. In June 1942, Peggy and her steady boyfriend of seven years, James Wright, decided to get married before he was sent to Europe. Although he was gone, Gilbert was kept busy, saying that during World War II, her band was working all the time in all different job settings. 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. In October 1944, before she left for Alaska, Gilbert met Kay Boley, and the two instantly became close, lifelong friends. When Gilbert and her husband got a divorce, she and Kay moved in together and continued out their lives as loving partners and supportive friends. During that time, there was "no presumption or discussion of a lesbian lifestyle," and Gilbert and Kay's lifestyle was accepted by their friends and family. When the war ended, Gilbert was back in Los Angeles trying to find jobs for her big band. Many women musicians, including Gilbert, lost their jobs after World War II because the women "had to move over and let [the men] take over where they left off." While Gilbert continued to play whenever she could, she began to work full-time for Local 47, doing clerical work. She was forced to organize a band of men and women after the war because there was a lack of female musicians. This band, called The Jacks and Jills, included Gilbert's brother Orval on drums and continued to perform until the 1950s. In the late 1940s, jazz began to develop into bebop, and Gilbert's bands became steadily old-fashioned. By 1949, Gilbert was in high demand as a secretary and served on many committees at Local 47. With this section of her life coming to a close, it was clear that "her skill as a saxophonist and bandleader, combined with business acumen, flexibility, and good humor, allowed her to make a living and support her family throughout the depression and war years." In 1951, Gilbert received permission from Local 47 to perform with Ada Leonard on KTTV television for a year.