This chapter investigates how military psychiatrists have analyzed the “waiting wife.” In 1968, an Air Force psychiatrist lamented that colleagues, faced with many “modern Penelopes who are unsuccessful in adapting to their husbands‘ absence,” had neglected this “important clinical problem.” This soon changed. Clinicians probed the “syndromes” they diagnosed in servicemen‘s wives during the latter years of the Vietnam War. Wives of POWs came under particular scrutiny, with researchers developing algorithms to forecast which POWs‘ marriages would survive. Media interest in POW spouses peaked with “Operation Homecoming” in 1973. When several returned prisoners‘ marriages collapsed soon thereafter, “Penelope” was again found wanting. This chapter links national anxieties about POWs‘ wives to broader figurations of female disloyalty. Dr. Emanuel Tanay‘s hypothesis of a “Dear John Syndrome” in Vietnam had already proposed in 1969 that women were sending more, and more vicious, Dear Johns to American men in southeast Asia than in any prior war. Veterans would soon amplify the charge that treachery on the home front, spousal and federal, had been unprecedentedly pervasive and injurious.