To claim that ethics and morality lie at the foundation of effective administrative praxis is neither new nor revolutionary--numerous studies have demonstrated that moral issues are embedded in the weave and texture of schooling and influence administrative choices. This paper explores the challenges, tensions and dilemmas new administrators experience. It is framed by the experiences of eight recently appointed secondary school vice-principals in a culturally diverse urban environment. A metaphor of epicycles is employed to describe the iterative cognitive, socio-emotional and moral pathways these individuals construct as they negotiate the organizational boundaries between teaching and administration. The article concludes with recommendations for sustainable structures that scaffold the moral developmental needs of newcomers.