In an era of education defined by standards and accountability, teacher retention continues to be a major factor contributing to student achievement levels. Particularly in under-resourced, Title I-funded schools the challenge of maintaining adequate staffing of highly qualified educators, especially in mathematics, remains a pressing challenge and obstacle towards learning outcomes. While ample research exists on the reasons for teacher attrition and movement out of the education field, limited accounts explore the inverse of this issue -- what causes teachers to continue working in high-turnover Title I schools? This qualitative portraiture details the lived experiences and stories of four secondary school mathematics teachers in a suburban urban school district in the northeastern United States, delving deeper into teacher retention challenges and job satisfaction through triangulation between survey respondents, in-depth interviews with additional ongoing informal conversations, and archival data. Ultimately, positive building-level experiences, especially career growth opportunities and an affinitive culture were found to be related to retention while negative experiences, such as feeling unsupported were often the "final straw" which resulted in staff departure. While weaving together the common thematic narratives of these teachers, I also juxtaposed the accounts of teachers who stayed and those who left proposing a "Tipping Point of Attrition" conceptual model which leaders can use to create favorable job conditions anchoring teacher retention against negative factors that contribute towards attrition and eventual turnover. [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.]