This paper discusses a qualitative study which examined students' problem-solving, metacognition, and motivation in a learning environment designed for teaching educational technology to pre-service teachers. The researchers converted a linear and didactic learning environment into a new open learning environment by contextualizing domain-related concepts and skills and providing ill-structured, collaborative problem-solving opportunities. The intervention called Learning Environments Approaching Professional Situations (LEAPS) took into account issues surrounding motivation and situativity that are of particular interest to instructional developers and design-based researchers. In this study, four classes were assigned as either traditional or LEAPS environments from which four cases were selected for further examination. The results suggested that the LEAPS approach was beneficial in supporting students' problem-solving, motivation, and self-reflections, but only under specific conditions. The implications for instructional design and motivation are discussed.