Representing issues discussed at the EduSummIT 2011 relative to essential conditions and barriers to successful technology integration, this article presents a systemic analysis of barriers that needed to be overcome for an information technology initiative (Remote Networked School project) to be successfully implemented. The analysis was conducted from an activity theory framework. Barriers were conceptualized as tensions that pulled constituents of an activity system or activity systems in opposite directions at four distinct levels of contradiction. Chains of tensions–pivotal actions that led to the overcoming of barriers were identified. Twelve exemplars illustrate how roles, policies and routines were transformed for necessary conditions to be in place in small remote schools. As emphasized by our application of activity theory, these conditions, which parallel the essential conditions formulated by the International Society for Technology in Education, can never be taken for granted by the educational agents of a specific setting. In the case presented, activity theory explains that the overcoming of barriers is an ongoing exercise as some tensions get resolved, reappear or give way to new ones.