Recruitment and retention of high-quality educators remains problematic throughout our public school systems. This is particularly so for teachers of minority-identifications and in high-poverty, high-minority urban schools and districts. Recent research concerning teacher longevity has typically focused on large-scale investigations of factors of educator dissatisfaction, normative treatments of urban school contexts, and the perspectives of early-career stage educators. Relying on classroom observations and in-depth interviews in a research context with which the researcher had intimate access and knowledge, this qualitative study attempts to interject insight into the extant literature by investigating and featuring the described sources of challenge, frustration, and critique as well as the sources of motivation, encouragement, and satisfaction for four African American women with twenty-five or more years of continuous classroom teaching experiences in a large school district serving high-minority and low-income core communities in a major Midwestern metropolitan area. Through a constant-comparative analysis of participant responses and grounded treatment of theoretical work concerning perseverance in teaching, findings in this study are framed across five themes of professional and personal (dis)satisfaction identified in the participants' responses: "competence," "commitment," "candor" and "acknowledgment," "agency," and "connection." Through these themes, normative presentations of professional "challenge" and "resilience," demarcations of sources of support and frustration, and professional-personal dichotomies encountered in the literature are critiqued and pushed. Findings from relevant, though, less-recent and smaller-scale research are bolstered. Through connections between deductive and inductive findings, two theoretical concepts are discussed as potentially useful frames for discussing teacher longevity and possible sources of encouragement: "life commitments" and "sustenance." [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]