When it comes to improving schools, context always matters (Murphy, 2013, p. 260). School leaders are "masters at brokering" (Murphy, 2013, p. 259) change. These changes are usually through the transfer of programs, interventions, and structures that worked elsewhere and pay little regard to the conditions and context that made them work (Murphy, 2013). School improvement reform will require "substantive systemic change" (Adelman and Taylor, 2007, p. 55) that considers the "current culture of schools and intended school improvements" (Adelman and Taylor, 2007, p. 56). This study will use a qualitative, multiple case-study methodology, a semi-structured interview protocol, and a document review to identify how school leaders in five, accredited high or mid-high poverty Virginia middle schools both identified and provided resources to address barriers to student learning. The instrumentation tool for this study was based on the learning or enabling components of the Adelman and Taylor improvement model (2008). The tool was used to qualify the school leaders' site-based school resource allocation and then analyzed for common themes. The study found that some learning or enabling supports were more represented than others. The study also found that there were three key leadership traits among school leaders who had effectively resourced the learning supports: instructional leadership; human-resource leadership; and culture and expectations leadership. Implications from this study include the need for further research on models for school improvement that require schools and districts to identify, plan, and provide for barriers to student learning. A second implication is the need for further study on leadership traits that might exist in school leaders who not only recognize but are able to inspire the implicit and explicit need to plan and provide for overcoming barriers to student learning. / Doctor of Education / The process of improving schools is important. The decision-making and school improvement structures that most schools employ is one that focuses mainly on classroom instruction with little regard to planning for students who may struggle because of outside barriers, like the effects of poverty, lack of exposure to background knowledge, or insufficient schooling and experiences. This study used a qualitative, multiple case-study methodology, a semi-structured interview protocol, and a document review to identify how school principals in five, accredited high or mid-high poverty Virginia middle schools both identified and provided resources to address barriers to student learning. The study used the learning or enabling components of the Adelman and Taylor improvement model (2008) to qualify the school leaders’ site-based school resource allocation and then analyzed them for common themes. The study found that some learning or enabling supports were more represented than others. The study also found that there were three key leadership traits among school leaders who had effectively resourced the learning supports: instructional leadership; human-resource leadership; and culture and expectations leadership.