This paper describes the organizational development of virtual learning in networked rural and other schools in New Zealand in 2011, specifically the obstacles that e-learning clusters of rural schools faced in their journey to maturity through the lens of the Ministry’s Learning Communities Online Handbook. Analysis of a nationwide purposeful sample identified three common barriers: a lack of a coherent vision; difficulty in sustaining necessary funding and resources; and a surprising lack of collaboration within and between clusters. Since 2011 critique of the maturity modeling has led to reinterpretation of the data through an evolutionary perspective, leading to new recommendations for strategic development of leadership capacity and an ongoing nationwide survey to inform such strategic change with digital technologies in education.