This study explores educational technology infusion in the U.S. school district context. We used a complex systems perspective to understand the interactions between the classroom (micro), building (meso), and organization (macro) system levels of a school district, offering insight into "how" and "why" certain permutations of tools, content, and practices are effective and impactful. We used comparative case study methods to understand (a) patterns in teachers' implementation of digital technologies in early elementary classrooms and (b) the organizational system that influences those patterns in one small school district serving a mixed suburban/rural community. Data were collected over 12 months, and included: elementary classroom observations, interviews with principals and district leaders, and student performance data. Our findings trace activities within and connections across levels of a district organization undergoing technology infusion. We found that district administration established human-centered leadership practices to facilitate instructional technology integration and principals maintained this leadership ethos in variable ways. Teachers leveraged technology for personalization and collaborative learning, and used robust classroom management routines to anchor complex instruction with young children. The findings highlight key considerations for system leaders, technologists, and policymakers; in particular, establishing a professional culture that offers widespread support for instructional experimentation.