We examined the utility of a technologically enhanced collective regulation system for improving students' collaborative sense-making processes, i.e., discussion quality, over time. Participants were 27 online undergraduate students enrolled in an introductory information science course. Students were divided into teams tasked with carrying out five online synchronous discussions and collective reflection activities in the system focusing on improving their processes over a ten-week period. Discussion quality was evaluated by a trained graduate student, using the same assessment rubric used by teams. Both qualitative and quantitative analysis techniques were used to examine teams' collaborative discussion quality and socio-metacognitive processes over time. Findings suggest teams significantly improved discussion quality and used the features in the system to do so. The results also suggested that while individuals were generally inaccurate in assessing their team's discussion quality, group assessment accuracy and identification of team's weaknesses improved over time in select areas.