The research design for this study focuses on examining the core issues and challenges when video games are used in the classroom. For this purpose three naturalistic contexts in Turkey were examined in which educational video games were used as the basis for teaching units on world continents and countries, first aid, and basic computer hardware and peripherals, in primary, secondary and higher education contexts respectively. Methods employed in the data collection include observing lessons, taking field notes, interviewing students and teachers, saving online discourse data, and collecting student artifacts and reflections. Findings identified issues related to (1) the design of the video game environment, (2) school infrastructure, (3) the nature of learning, the role of the teacher and classroom culture, and (4) engagement.