This article describes the development of a technology-enhanced self-regulated learning (Te-SRL) environment designed to foster students’ SRL of complex science topics. The environment consists of three components, one of which is a specially designed computerized system that offers students a choice between different types of scaffolding and encourages them to make multiple choices regarding the paths that they take when planning their learning. We describe a three-year mixed-methods study aimed at observing learners’ use of SRL processes when learning in the Te-SRL environment. This article focuses on nine case studies that were selected from 630 seventh-grade students who participated in the study. Data were obtained from assessment tasks, self-evaluation forms, think-aloud protocols, and interviews; data were traced from the computerized system. The findings suggest that students can improve over time in regulating their learning and in utilizing learning skills in a computerized system when provided with opportunities to practice, along with scaffolding. Many students, however, did not take full advantage of these scaffolding opportunities and seemed to lack the high-level skills needed for seeking information on the Internet. These findings underscore the importance of developing a culture of learning with technology-enhanced learning environments and scaffolding SRL in such environments.