This article offers a capacious view of technology to suggest broad principles relating technology and language use, language teaching, and language learning. The first part of the article considers some of the ways that technological media influence contexts and forms of expression and communication. In the second part, a set of heuristic questions is proposed to help guide language teachers and researchers in determining how to incorporate technology into their teaching practice or research agenda and evaluate its suitability and impact. These questions are based primarily on the goal of helping learners to pay critical attention to the culturally encoded connections among forms, contexts, meanings, and ideologies that they will encounter and produce in different mediums, both traditional and new.