Building and sustaining a school and district culture that has a technology "growth mindset" and the implementation of processes that support a technology-specific culture in which, "the role of the leader is to ensure that the organization develops relationships that help produce desirable results," would ensure that teachers and principals collaboratively and collectively acquire specific knowledge and skills that directly support the leadership roles, as well as assist in meeting the varied challenges that most school leaders face when leading e-learning and virtual campuses. Furthermore, the key to creating buy-in for technology, especially e-learning and virtual schools, will require that university/principal preparation programs work collaboratively with local school districts and national/state technology organizations to build capacity of future administrators and teacher leaders. This is not to say that local and national organizations are not focusing on professional development, but the focus needs to include specific training that ensures that school leaders acquire very specific knowledge and skills on how to reculture their schools and districts as e-learning and or virtual campuses. In addition, professional development for school leaders that deals specifically in addressing first and second order changes is a must. Finally, the implementation and sustainability of technology across a school would not be possible without development of an open climate and culture. In this article, an exploration of technological trends documented by organizations and researchers (what has worked, what hasn't) in efforts thus far to create and sustain virtual schools at the PK-12 levels is presented. Additionally, the importance of leadership support is reviewed--in particular, the role of the principal and superintendent and how they influence the sustainability of online learning and the change process. A focus on the challenges administrators face and the roles they should assume when implementing and sustaining online technology for instruction are developed. These challenges include the principal's leadership role, the need for new kinds and content of professional development, and what appear to be emerging best practices for those interested in creating and sustaining the new teaching and learning environment.