This essay examines the school leadership experiences of an infant school head teacher in Birmingham, England, during the Second World War. Drawing on the letters of Dorothy Walker, the essay offers insights into school leadership wartime deprivations. The impact of an international war on the home front was not head teacher Dorothy Walker's only challenge. As the youngest and one of the few women head teachers in Birmingham, Dorothy Walker struggled with the traditional masculine hierarchy of the local educational system and with traditional social and familial gender roles. Dorothy Walker also battled with a traditional educational school culture as she promoted progressive educational practices. These three challenges - the war, gender relations, and progressivism - are referred to as 'Dorothy's Wars', or the battles that she faced as a woman school leader in Birmingham during the early years of the Second World War.