Through the utilization of school discipline policies, millions of students nationwide have been harshly disciplined and/or removed from the regular school setting – with lasting impact on both students and their communities. With regards to discretionary school discipline policies, those tasked with implementing them – both at the district and school level, as well as in the classroom – could have a real influence on the outcomes of the policies, due to the basic viewpoints and interpretations that each policy administrator brings to the table. In other words, the way administrators make sense of discipline – including their interpretation of its purpose or efficacy – may be a key factor in the policy implementation process and in policy outcomes (including the over-use of discretionary policies and an over-reliance on more punitive consequences), something to be considered by those examining implementation and outcomes. This study explores the role of principals’ and assistant principals’ own viewpoints in the execution of such policies – specifically, in an urban school district in Texas – which no research has solely and fully touched on in Texas prior to this study. This researcher has sought to examine and explain the potential relationships between the following: a) middle and high school administrators’ interpretation of discretionary school discipline policies (including administrators’ views about purpose and efficacy to provide this researcher with context for each administrator); b) these administrators’ understandings about the factors (“affinities”/themes) that may influence their actual implementation of discipline policies (including both school-specific conditions and student-specific characteristics); and c) the rate of disciplinary actions taken by schools, in comparison to the predicted rate of such action. To provide an examination and explanation of administrators’ interpretation of, as well as the drivers behind, their implementation of discretionary school discipline policies, this researcher has utilized a qualitative research method highly informed by Interactive Qualitative Analysis (IQA), which also incorporates a quantitative data component. This researcher hopes that this study will allow for a broadened discussion of alternative ways of thinking – including considerations of effective alternative programming and strategies – that administrators can employ when dealing with students determined to be problems in the classroom. / text