This study intended to answer the research question: “What are the necessary working conditions for promoting retention identified by teachers within a high-performing charter network?” Through the analysis of 195 survey responses, 19 one-on-one interviews, and one focus group, one overarching factor—an Ailing Culture—connects the four interconnected themes: Cognitive Dissonance, Replaceability, Absence of an Expectation for Continuous Learning, and Weak Communication and Lack of Transparency. These issues, if eliminated or at least mitigated, might lead to higher retention of teachers. These findings point to factors that might be causing teachers to lean towards leaving this particular charter school network; in order to reverse this potential trend, the issues embedded within these themes will need to be addressed.