The aim of this work is to introduce a case study to test a context modelingprocess proposed to help teachers/tutors make an adaptive tutorial decision when acting by TEL (Technology Enhanced Learning) environments. It attempts also to involve teachers as designers in the engineering process of a TEL system development and to support their activity of auto regulation regarding students’ guidance and assistance. This intention leads to improve teaching strategies as well as to enhance the quality of the learning objects and the learning scenario itself. In fact if the TEL system isalready adaptive, by means of this approach its improvement is fostered. If it is not, the process will support its iterative transformation from predefined to adaptive. Aspects of the language UTL (Usage Tracking Language) used for the calculation of indicators that support the decision making during the tutorial action, are introduced to reveal the observed uses of the descriptive pedagogic scenario and their semantics, including the definition of the observation needs and the means used for data acquisition. The Problem Based Learning strategy is applied to develop in students, best practices in Java programming.