The need for equitable school leadership has emerged as an educational priority in recent years as researchers continue to uncover a complex system of biases and structural inequities that impact the engagement of our most vulnerable learners. These inequities are especially prevalent in certain subgroups, including Black, Latino, English Learners, Special Education, and economically disadvantaged students. Moreover, this equity and achievement gap has been further exacerbated by the reverberating influence of the recent global COVID-19 pandemic. The combination of culturally and contextually responsive leadership practices holds promise as K-12 school systems struggle to engage with the increasingly diverse needs of our students and communities. Aside from the impact of classroom teachers, school leadership has been identified as the most influential school-based factor in promoting student achievement. To that end, this qualitative study focuses on school and district-level leadership practices that promote culturally and contextually responsive outcomes in support of culture, pedagogy, and student engagement. Guided by established engagement theory and successful school leadership frameworks, this study has identified a combination of emerging and interconnected leadership practices with the capacity to support improved engagement outcomes for marginalized populations, including the English Learners and Alternative Education students at the center of this cross-context study. The significant leadership practices identified in this study include: relevant, meaningful, and inclusive curriculum; attending to social emotional learning and needs of students; and a contextualized approach to school-based leadership in support of curriculum, pedagogy, and professional learning. This study concludes with implications for practice and future study. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]