In the 40th Annual Phi Delta Kappa/Gallup Poll of the Public’s Attitudes toward the Public Schools, Americans rated discipline as the second largest problem facing public education (Bushaw & Gallup, 2008). This poses a substantial problem for administrators as they strive to employ school reform policies, address public demands and meet the needs of contemporary students. A review of literature revealed a large body of research which examines disciplinary practice; however, it also showcased a literary gap regarding administrative disciplinary philosophies. This multiple case study highlights disciplinary philosophies possessed by five secondary school administrators. Analysis included utilizing the Administrator Discipline Facilitation Continuum; an adapted discipline continuum developed to analyze administrator disciplinary philosophies. The versatility of the continuum is discussed, as well as implications for its use and future development.