This paper reports results from a case study focused on understanding student practices regarding production-oriented problem-solving with digital media. Thirty-seven students participated in an elective curriculum called, "Techno Savvy," a nine-week course focused on student exploration of global issues, and designed around Web 2.0 tools. Socio-constructivist theory provided the theoretical lens to write and study the curriculum. Complexity in student practices using digital media tools to determine critical thinking is highlighted. Data were analyzed for patterns observed in student practices, video, artifacts, oral, and written work. Results suggest that student interaction and practices afforded by tools and content within the curriculum encourage critical thinking. This study implies a need for further classroom research linking pedagogical approaches with digital media to critical thinking and achievement.