In the United States, there are more than 600 alternate route programs, including Teach for America, providing school districts with hundreds of new teachers every year (Feitritzer, 2009). The shortage of highly qualified teachers, particularly in urban school districts, is an ongoing concern in education and one not easily solved by investment in recruitment and hiring given that in urban school districts half of the new teachers will leave within three years (Ingersoll & Smith, 2003) Despite evidence of the challenges of teacher retention and attrition, many teachers, including those in alternative certification programs like TFA, decide to remain in the classroom. The current study focuses on the experiences of 20 TFA alumni who are currently in the classroom five or more years beyond their two-year agreement date. Findings from the current study show that participants shared similar experiences to their traditional teacher counterparts. However, many of their reasons for staying in the classroom were connected to the relationships built with students. Participants in the current study also focused on the different relationships formed with other TFA teachers, TFA staff, and key staff members in their respective schools. It is the general recommendation of this study that the training for TFA teachers become more personalized with an emphasis on student relationship building as well as meeting the needs of each new cohort member based on where they are in their career stage. These recommendations and other implications for future research and policy recommendations are discussed in detail. [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.]