Within digitally-supported learning environments, learners need to observe themselves so that they can reflect on their strengths and weaknesses and take a step toward autonomous learning. Within the scope of this research, a technology and analytics enhanced assessment environment in which students can assess themselves was implemented and tested. In order to determine N = 108 students' ability to use the assessment environment, behavioral patterns were determined based on their individual characteristics, system interactions, lesson performances, achievement motivation, confidence, and study interest. Findings indicate different system usage and behavioral engagement with the assessment system. The outcomes of this design-based research project indicate hints on how such assessment systems can be made more effective in future implementation stages.