This paper describes the fit between educational technologies and teacher views and pedagogies in light of two recently completed research projects. These studies focused on observed pedagogies associated with the classroom-based use of two learning technologies: digital video (student-generated), and interactive whiteboards. The paper considers the use of these two technologies from a sociocultural perspective, recognizing that the nature of tools and the nature of societal use of these tools are mutually dependent. Questions are raised about how the inherent nature of different technologies might shape different learning experiences and outcomes and whether certain technologies fit better with some pedagogical approaches than others.