Since the 1954 Brown v. Board of Education ruling against school segregation, Black women teachers (BWTs) have had perpetually high rates of attrition, despite their legacy of providing high quality, emancipatory education (Acosta, 2019; Carver-Thomas & Darling-Hammond; 2017b; Dixson, 2003). While scholars have sought to understand BWT attrition and remedy the issue through policy and practice recommendations, the phenomenon persists. Thus, the purpose of this study was to contextualize the attrition of critical BWTs to better understand the factors that would support their sustainability in urban schools. While retention efforts aim to keep teachers in the profession, it is necessary to instead emphasize this population’s sustainability, which is more complex and calls for "schools and other educational institutions [to] become more welcoming and supportive places for them, where their professional practice can be cultivated over time" (Mosely, 2018, p. 269). Specifically, I investigated (a) the relationship between Black women’s intersectional identities and their experiences as critical educators in urban schools, (b) the compounding factors that led to their ultimate departure, and (c) the complexities of their decision to leave the profession. Using Black feminist thought and cognitive dissonance theory as my framework, I employed sista circle methodology to study fifteen critical Black women teachers who left the profession. Thus, each participant engaged in one of three sista circles, which were my primary data collection method, in addition to an individual pre-interview and a final written reflection. After analyzing my data through an iterative process of multiple data readings, memo writing, open coding, and axial coding, the findings revealed three major themes: instinct vs. opposition, commitments vs. personal needs, and dissonance-reduction strategies. Instinct vs. opposition highlights the participants’ convictions about practicing emancipatory pedagogy, despite their efforts being sabotaged by various barriers. Commitments vs. personal needs captures the participants’ dedication to their students, which conflicted with personal needs that required them to leave teaching. Finally, dissonance-reduction strategies depicts how the participants worked through the cognitive dissonance (i.e., discomfort from realizing contradictions between values and actions) resulting from their beliefs about teaching and decision to leave. These themes offer rich context and a complex narrative of why critical BWTs love and leave the classroom. Chapter 1 of this dissertation provides a description of the problem addressed by this study, a thorough description of the conceptual framework, and an overview of the study. Chapter 2 provides a comprehensive overview of the literature regarding the history, significance, and attrition of critical BWTs. Chapter 3 details the methodology used, and Chapter 4 presents the findings through three major themes and twelve subthemes. Finally, in Chapter 5 I situate this research in the broader literature, highlighting this study’s contribution to the field, and offer recommendations to key stakeholders, including policymakers, educator preparation programs, school administrators, and BWTs to make meaningful impacts on the sustainability of critical BWTs in urban schools.