The purpose of this qualitative, multiple case study was to explore the practices and behaviors of successful Latin@ principals in high-need Texas middle schools focusing on the following three areas: learning, leadership, and context. Varying qualities of leadership essential for leading high-need middle schools coupled with contextual factors such as policy and community were examined. More importantly, this research sought how successful Latin@ leaders promoted a culture of learning in high-need middle schools with a focus on English learners (ELs). High-need schools are defined as those presenting a context that challenges the success of students. The study on leadership in high-need schools focuses on an investigation of strategies principals in these schools may employ and determining ways in which high-need school leaders are prepared and supported. Factors affecting the condition in high-need schools may include: (a) student and community characteristics (e.g., ethnic minorities, mobility, poverty, non-native language speakers), (b) student performance (e.g., math and reading scores, graduation rates, attendance), and (c) other factors (e.g., teacher and leader turnover, staff morale, student engagement). The context of schools matters and effective leaders in high-need schools must be able to lead using contextually appropriate responses. Two Latina principals serving in high-need middle schools, in Texas, enhanced organizational and individual performance that fostered a culture of learning and equity for ELs as they supported teachers and created inclusive learning environments for students and families.