In this case study the participants, 21 undergraduate students, self-evaluated and developed their self-regulated learning using an on-line self-report instrument (IQ Form) modified from MSLQ (Pintrich et al., 1993). Additional data were collected by focused interviews, which were content analysed and deductively analysed using Ruohotie’s (2000) categorisation of naïve and skilful learners in self-regulation. Participants’ self-reports and interview analyses were compared and revealed coherent results about the stage of participants’ SRL. The on-line self-evaluation and tutoring system designed to enhance self-regulation activated participants to self-study, which is crucial for the initial stage of self-regulation to develop. It was shown that for naïve self-regulators enhancing assignments should be built into the course tasks and they need teachers’ guidance to benefit from the on-line tutoring material. The skilful self-regulators were more motivated to develop their learning strategies and voluntarily went into depth on these tasks and took advantage of the on-line system. By applying IQ Form, almost all students realised that they themselves could have an influence on their learning, but in practice naïve SRL students did not improve their strategies. An on-line tutoring system is useful for all, but pedagogical tailoring best promotes different student’s development in SRL.