This study examines urban school leaders and their decision-making around external partnership relations in resource-constrained contexts. I employed a case study design guided by sense-making and cultural responsiveness to highlight behaviors that contribute to successful partnership work (Ganon-Shilon & Schecter, 2017; Khalifa, Gooden & Davis, 2016). To do this work, I conducted this research in three predominantly Black schools in the Detroit Public Schools Community District. Using in-depth phenomenological interviewing (Seidman, 2007), I worked with three Black school leaders, and four members of the Volunteer Corps volunteer organization to understand the inner workings of the partnership relationship and how different factors influenced implementation school-wide. Volunteer Corps is an organization that works with urban school districts to provide 10-15 full-time volunteers to work in district-identified schools. The school leaders talked at length about their process of incorporating other external organizations into their schools' operational framework. The findings from this study suggest that school leaders lean heavily on sensemaking processes when working with external partnership organizations. School leaders have to piece together an understanding based on information they gather from both formal and informal sources. Also, school leaders in the study discussed how their preparation to become principals had some gaps regarding external partnership work. Some findings suggest that when school leaders maintain partnerships with organizations that provide volunteers, the racial makeup of volunteers has a variety of effects on predominantly Black school contexts. For example, the school leaders in the study had to devote additional time to conduct cultural responsiveness training to prepare white volunteers to work with Black students. Last, school leaders named several benefits and costs associated with partnership work. While some benefits seemed obvious (i.e. additional money, additional human capital), there was some complexity and nuance in the benefits and costs. I analyzed these findings through a lens of sensemaking, to understand the process, and Critical Race Theory, to speak to the context of the communities and schools. Principals can learn from this study because it provides examples of the ways school leaders in urban school contexts have navigated the work of external partnership work. Leadership preparation programs could also benefit from understanding the mechanics of external partnership work to better prepare prospective principal candidates for the work of engaging with and maintaining resources from organizations. This study could also inform policymakers, as the findings have implications for the notion of equity, and the conditions that cause the creation of partnerships with external partnership organizations. [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.]