There is a looming crisis in attracting, supporting, and retaining principals in Australian schools. Issues of work intensification and extension, coupled with the emotional intensity of leading a school, have resulted in fewer people aspiring to the principalship. It is increasingly difficult to find leaders for “hard-to-staff” rural schools, resulting in higher rates of principal turnover and more inexperienced leaders taking on the role. These circumstances have direct consequences for student achievement, community engagement, and teacher retention. This chapter draws on a national study of current, former, and aspiring Australian principals to explore their experiences within the role. In particular, the chapter focuses on experiences of principal wellbeing, support, and subsequent retention within the role. These experiences are analysed in light of policies relating to principal recruitment and retention, and rural education more broadly. The findings reveal the challenges and joys of leading rural schools, as well as the types of support that would encourage principals to remain within their schools or the wider profession for longer. The chapter suggests that targeted development, systemic support, and meaningful reductions in workload would be effective approaches towards promoting attraction and retention for principals.