In this article, it is argued that learner's individual activities and interpretations in new learning environments have not been adequately analyzed. The analyses of students' social and motivational interpretations of interaction during classroom teaching and learning are reported. The interactive learning was organized according to the principles of a cognitive apprenticeship and applied to a technology-based learning environment. The purpose of the learning task was to promote the mediation of modern technological thinking and problem-solving skills for 7th grade students in a LegoTClogo environment. An on-line method was developed for step by step analysis of students' social interpretations and motivational orientation during the learning process. In Study 1 the focus was to describe how interaction based on cognitive apprenticeship in a complex technology-based learning environment affects the students' situational motivational and emotional interpretations. It is demonstrated what are the possible processes to appear among the students by describing eight cases. The results show that only some students interpreted tasks and teacher's activities in the anticipated direction of the cognitive apprenticeship model. In Study 2 six case-based descriptions demonstrate how students with different orientational tendencies in a traditional classroom learning develop their motivational orientation and coping strategies during the experimental lessons. For that purpose the students' motivational orientations in traditional classroom lessons were evaluated with paper and pencil tests. The results indicate that the cognitive apprenticeship and technology rich environment may maintain the student's tendency toward task orientation and even direct some students toward task-orientation. It is concluded that the same instructional arrangements in two studies were interpreted differently and led to different cognitive and emotional processes among individual students. The results call for a discussion on more detailed considerations of the complex interactional bases for individual students' motivation and new instructional design.