The 21st century places significant demands on our educational system. It is an opportune time to re-imagine the mission, operations, and skills expected of school district offices. The focus of this study was on the school district's role in strengthening principals' instructional leadership capacity for improving educational outcomes. Using a case study design, interviews were conducted with 10 principals and 14 district officials in one school district. The findings showed that district officials placed instructional leadership at the core of their role in their interactions with principals. They continued to monitor curriculum delivery and provided reports but also assumed a mentoring approach in working with principals. The study further highlighted that principals did not always implement recommendations to improve instruction at schools as they felt overwhelmed by work demands. Principals expressed the need for professional development tailored to their instructional leadership roles and on-site workshops. The findings indicate that there is aneed for greater communication between principals and district officials where principals can openly deliberate issues related to instructional leadership confronting their schools with a view to problem solving. Moreover, district officials could enable the sharing of best instructional practices among schools.