This paper outlines a four-year study of a preservice education course based on a socio-constructivist research framework. The preservice English Language Arts course focuses on critical literacy and teaching for social justice while employing digital technologies. The research study examines two concepts across all aspects of the course: 1) new literacies and multiliteracies; and 2) technology-supported transformative pedagogy for social and educational change. While the authors originally undertook the study to evaluate separate assignments of the course, the lens of the two themes has provided an opportunity for a scholarly review of their teaching practices. Research data include three course assignments over a 2-year period; an open-ended survey; and focus group and individual interviews with pre-service teachers. The authors discuss some of the affordances, challenges, and learnings associated with preparing teachers to teach critical literacy in a digital age. They also consider the development of critical literacy skills which encourage preservice teachers to bring their literacy histories and assumptions to the surface, examine them critically, and consider social justice alternatives.