This article examined, thought a Cultural Historical Activity Theory lens, how immersive- or pervasive environments and pedagogical agents could more easily support social collaboration as foundation of contemporary learning theory. It is argued that the fundamentalism-liberationism contradiction (learn from versus learn with technology) is no longer justifiable as contemporary technology tools (pervasive/immersive environments and agent technology), the understanding of social networks, and recent neuro-science discoveries negate instructional design philosophies and innatist positions. The use of an activity lens allowed for identification of a number of educational technology design principles including explication of ideological positions, designs for contradictions, acceptance of a post-modern position, designs to overcome homophilic associations, and use of complex real-world learning activities.