This article describes the evolution of communication technologies, accompanying transformations in everyday communicative activity, and pedagogical possibilities these tools support in second and foreign language (L2) settings. We begin with an overview of synchronous computer-mediated communication (SCMC) and uses of the Internet to mediate intercultural communication for purposes of L2 learning. We then describe generational shifts in Internet technologies and their proliferation and uses, with the majority of our efforts focused on contemporary environments such as blogs, wikis, podcasting, device-agnostic forms of CMC, and advances in intelligent computer-assisted language learning (ICALL). Throughout, we engage in a discussion of praxeological fusions of various media technologies and the implications of this nexus of practice for the transformation of what it means to teach, learn, and communicate in L2 contexts.