Critical approaches to policy suggest that policy, even in the most apparently democratic polity or institution, codifies and extends the interests of those who disproportionately wield power (Levinson et al., 2009). While many people are involved in conversations and decision-making processes related to the implementation of grade retention or promotion policies, the final decision is made at the school level. Critics of grade retention, meanwhile, also warn that retained students may be harmed by stigmatization, reduced expectations for their academic performance on the part of teachers and parents, and the challenges of adjusting to a new peer group (Schwerdt et al., 2017). The purpose of this mixed methods study was to examine how school leaders developed and implemented retention policy for the fastest growing student populations in the United States: English learners (ELs) (Rubio, 2014). I conducted a survey of 62 elementary school principals in one large suburban school district in Virginia. Preliminary analysis of the survey responses that was used to purposefully select a subsample of principals that engaged them in semi-structured interviews that deeply explored how school leaders made sense of grade retention policies for ELs. In particular, I focused on if and how school leaders' personal characteristics and school context influenced how they made sense of and implemented retention policy for ELs in their schools. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]