This study investigated how high school principals make meaning of the ethical issues they face. Sixteen Iowa public high school principals were selected by gender and district size. Each participated in a one-hour face-to-face interview with the researcher who had five years of building-level administrative experience at the middle and secondary level.;Narratives were analyzed identifying major categories of educational beliefs and values, ethical issues, and ethical dilemmas. Kidder's Resolution Principals of Ends-based Thinking, Rule-based Thinking, and Care-based Thinking were evident as participants balanced personal and professional ethics and described decisions made. Which principles were used most often and in what situations varied with no patterns emerging by years of administrative or teaching experience, gender, or district size. It was found that the three Dilemma Paradigms of Individual versus Community, Short-term versus Long-term, and Justice versus Mercy together play a consistently central role in how high school principals manage discipline issues. Principals reported a frequent overlap of discipline issues, special education, and decisions about allocation of resources. The Dilemma Paradigm of Truth versus Loyalty was reported to occur less frequently, but to be exceptionally difficult, disrupting communication and interfering with professional and emotional support. No gender differences were found in how school administrators face ethical issues in schools. However, what issues were identified as ethical issues did vary by gender. Zero of eight male participants compared to six of eight female participants identified gender in the daily work life of school administrators as an ethical issue.;There is a disjunction between administrators' expressed need to talk and constraints not to do so, increasing feelings of isolation. This is often due to issues of confidentiality, but also to the need to maintain the school and district in a positive light. Principals in medium and small districts were likely to report a cautious communication style of self-silencing because of the multiple overlapping social relationships in smaller communities.;The concept of shared reliance is discussed related to the social nature of learning, the value of egalitarian co-mentoring, and learning in cohort groups.