Teachers are leaving the field of education at a rate of over 50% in the first five years of teaching; the rate of departure is up to one third higher in an urban setting. This pattern has increased steadily over the last thirty years. This study explored this situation in the hope of identifying strategies to decrease attrition and promote retention. It reviewed the relationship of three variables (grit, job satisfaction, and cultural competence) to teacher length of service in an urban school district. Differences in scores on the three independent variables were examined between regular and special education teachers within the sample. Additionally, the study investigated whether the statistically significant variables could produce a model for predicting teacher length of service. The sample included 102 regular and special education teachers from one medium-sized, urban K-12 school district in southeastern Pennsylvania. The research was grounded in resilience theory where predictors were studied for their ability to be considered mechanisms that could alter the risk impact of teacher attrition in urban schools. The results of the research indicated that job satisfaction and cultural competence have a statistical relationship with teacher length of service in the district studied. Special education teachers demonstrated a statistically significant higher job satisfaction rate than the regular education teachers within the sample. Implications for educators based on the results of this study include improving training for school leaders on the importance of job satisfaction and Personal Involvement of staff within the school community. The role of professional development for pre-service teachers, current teachers, and school leaders on unique aspects of the urban education setting have also emerged. [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.]