The challenge of obtaining an education is more difficult for students living in poverty. Given the responsibilities of educators to support these students and their unique needs, it is critical to identify their level of awareness of what they struggle with, and to provide guidance on how to develop strategies to utilize to support these students and their families. This study sought insights from educators at a large urban school in the Midwest (N=9) to identify challenges and best practices, as well as an understanding of their knowledge, regarding students living in poverty. Utilizing a theoretical framework of Transformational Leadership (Burns, 1978) and guided in qualitative practices by Creswell (2014), this study utilized email interviews to develop intimate rapport with participants and to give them adequate space to opine. All the participants are educators serving a high-poverty student population. Because of the primacy of education as a pathway out of poverty, it is important to identify any supports that educational leaders can provide to students struggling with poverty. The results of this study, which identified themes around institutional and family support among others, were used to develop a training for educators and leaders to guide them in supporting students living in poverty. [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.]