This chapter discusses the cultural transformation that world language learners can undergo when they engage with native speakers in virtual environments for autonomous interaction. Davidson (2010) outlines similar benefits for learners during variable-length study abroad programs; however, for many learners, access to study abroad is not feasible, practically or financially. Alternatives to study abroad experiences can be created using online resources and virtual communities of native speakers. Novice-level intensive courses and Advanced-level content courses in Russian provide instructional models. Portfolio and journal materials provide qualitative evidence of transformative experiences that learners undergo as they engage in mediating authentic artifacts and become increasingly culturally proficient.