This study is aimed at understanding the circumstances that contribute to teacher retention and attrition in urban schools in the Southwestern United States. Harris et al. (2019) reported that at the national level, 16% of all teachers attrit yearly. Attrition contributes to the increasing teacher shortage problem that many districts face. The purpose of the study, guided by Chris Argyris' organizational theory, examined the circumstances that contribute to the attrition of highly qualified teachers and the extent financial incentives are linked to the retention of highly qualified teachers. This qualitative phenomenological study involved 9 teachers, interviewed with a researcher designed interview protocol, who are employed in urban schools serving elementary, middle, and high school campuses, who received a financial incentive as a supplement to their base salary within the past 5 years. Participants discussed circumstances they encountered through their lived experiences working as a classroom teacher may have influenced their decision to remain or stay with a school. An analysis of the data revealed that financial incentives are not the primary reasons teachers remain in or leave a position. Other factors, such as working conditions, leadership and support outweigh the attractiveness of small, unsustainable financial incentives. The researcher found that if financial incentives are offered as an enticement for retention, they should be substantial and sustainable. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]