This investigation aimed to examine how self-regulation processes occur during tasks involving information seeking on the Web. Another objective was to understand how high school students grasp opportunities to develop self-regulated learning within a Web environment and how they perceived this process. This study presents two case studies where interview tasks and stimulated recall were used to highlight the complexity involved in self-regulated learning processes and to promote the development of self-regulatory skills at a metacognitive and motivational level. Results from cluster analysis revealed how students appropriate options that allow them to make choices as they actively participate in the construction of learning and understand how self-regulated learning processes occur. Specifically, the students involved in the case studies first analyzed the task's instructions and later, regulated their decision making processes throughout the task depending on the quality and reliability of the information they retrieved from the Web. These processes involved dynamic information seeking where students went back to the Web as they found necessary in order to obtain further information or to clarify doubts so as to complete the task's demands and reach the task's defined objectives. This study contributes to the discussion of assessment tools that capture the multidimensionality and dynamics of the processes involved in the self-regulation of learning and allow for an awareness of the processes adopted