Background: In the 40th Annual Phi Delta Kappa/Gallup Poll of the Public's Attitudes Toward the Public Schools, Americans rated student discipline as the second largest problem facing public education. This poses a substantial problem for administrators striving to employ school reform policies, address public demands, and meet the needs of contemporary students. Purpose: A review of the literature revealed a large body of research that examines disciplinary practice; however, it also showcased a literary gap regarding administrative disciplinary philosophies. Research Design: This multiple case study highlights disciplinary philosophies possessed by five secondary school administrators. Analysis includes utilizing the administrator discipline facilitation continuum, an adapted discipline continuum developed to analyze administrator disciplinary philosophies. Conclusions: The versatility of the continuum as well as implications for its use and future development are discussed. (Contains 1 figure and 1 table.)