The purpose of this study was to investigate the potential use of Second Life (Linden Labs, 2004) and Skype (Skype Limited, 2009) as simulated virtual professional development tools for pre-service teachers seeking endorsement in teaching English as a Second Official Language (ESOL). Second Life is an avatar-based Internet program that allows end-users to interact, using audio and chat features, with a digital representation of themselves (an avatar). Skype is an Internet-based video conferencing program that allows users to see each other by way of a webcam. Of particular interest to this study was how a group of 12 pre-service teacher education students internalized professional knowledge and if that knowledge was actually transferred into active teaching practice and professional identity development. To investigate this knowledge transfer, an exploratory case study (Yin, 2008) was conducted framed around the theories of sociocultural constructivism (Kanuka & Anderson, 1999; Vygotsky, 1978) and critical pedagogy (Freire, 1990). The components of one module from the ESOL II course that addressed hegemonic curriculum and teaching practices were recreated in Second Life and Skype or analysis. Using within-case analysis (Miles & Huberman, 1994), vignettes (Ely, Vinz, Downing, & Anzul, 1997; Spalding & Phillips, 2007), and tallied collaborative utterances (Erben 2001), developmental progressions among the pre-service teachers were examined from the beginning to the end of the module and were evaluated for their relevance to knowledge transfer and self-regulation. The interactions were also examined for instances of amplifications and reductions of pedagogic practices (Erben 1999) through collaborative dialogue (Bakhtin, 2006; Erben, 2001; Wertsch, 1991). The findings of this study suggested the positive potential of using Second Life and Skype to enable self-regulation and pedagogic transformations to occur among the participants with appropriate considerations acknowledged for the teaching audience, developmental goals, and venue of instruction.