A randomised controlled trial was designed to test an Internet-based interactive application as a stand-alone support for the development of self-assessment skills among second-year dental students at the Faculty of Dentistry, University of Malmö, Sweden. Fifty-two students were randomised into an experimental (n = 26) and a control group (n = 26). Both groups went through four identical learning cases in elementary clinical Periodontology during a period of 1 month. The experimental group received the cases with the interactive software, while the control group received them through a static web page. After the end of the learning phase, both groups were assessed blindly by two assessors during the interactive examination methodology. There was a moderate agreement between the two assessors, but both failed to find any significant differences between the two groups with regard to self-assessment skills and overall performance of the students. Students positively received the Internet support, but several attitude differences were observed between the two groups during the study. Time on task and competence with computers were positively correlated to assessment results for both groups. On the basis of these findings, it remains unclear if computer-based applications with automated feedback can constitute an effective remedial support for the improvement of self-assessment skills of students. In addition, for such applications to be successfully accepted, two factors are critical: students must have a clear perception of the benefits deriving from the use of the software and the use of the software should be integrated in the curriculum, replacing some of the existing workload.