This paper focuses on the design and implementation of an innovative technologically mediated intervention for argumentation pedagogy in two classes comprising 17- to 18-year-old students in Singapore. The design research involves integrating the "Second Life" immersive virtual environment and web-based scaffolding through a customized structured argumentation board into a language-based curriculum at the pre-university level (Grade 12), the General Paper, which emphasizes argumentation and critical thinking. Of specific interest in this paper are the processes and factors that impact both the technical aspects of implementation and pedagogical findings. It discusses the benefits and drawbacks arising from the design, planning and implementation of both platforms of technology into the curriculum. Recommendations to overcome problems identified and suggestions for future research in the field are proposed. (Contains 5 figures.)