In this paper we discuss the use of speculative design as an approach to developing technological fluency. We provide overviews of technological fluency and speculative design, trace their conceptual connections, and then outline the use of a speculative design approach to technology fluency programs, providing an example from a current project. We then conclude by discussing how a speculative design approach can extend the idea of technology fluency towards new directions: broadening common understandings of the practices of technology development and adding a dimension of criticality.