Every August, districts face pressure to ensure students and staff have timely, secure, and equitable access to digital learning tools. As digital ecosystems become more interconnected, breakdowns in communication, rostering, provisioning, or vendor coordination can disrupt teaching and learning. This interactive session shares one district’s journey from reactive troubleshooting toward a more coordinated and sustainable approach to student data readiness. Participants will explore how cross-functional teams mapped systems, redesigned timelines, clarified responsibilities, strengthened communication structures, and identified common failure points in the back-to-school onboarding process. Attendees will leave with practical strategies, planning ideas, workflow tools, and lessons learned to support more efficient, collaborative, and equitable back-to-school transitions.