Internet has become one of the most important information sources for students’ personal and academic life. In addition, the World Wide Web is receiving increased attention in education because of its potential to support new forms of learning. However, using the information from the net for learning requires the development of a set of abilities such as searching and tackling information from the Internet to find solutions of a problem—this set of abilities is called Information-Problem Solving (IPS) skills. The main objectives of this study are the following three: first, to provide a detailed description about how secondary students solve an IPS task; second, to identify key IPS skills, sub-skills, and regulation activities that have more incidence upon students’ success to solve a problem using digital information on the Web; and third, to use this information to draw educative guidelines to design web-based instructional process and foster IPS in secondary classrooms. In-depth analyses of quantitative and qualitative data of a multi-case study allowed us to identify distinctive patterns and sequences of IPS skills used by students to solve a task. Furthermore, IPS skills (defining the problem and search for information), sub-skills (specifying search terms and selecting results from a SERP), and regulation activities (orientation on the task, monitoring, and testing) were identified as key skills which have more incidence in students to solve successfully IPS tasks to learn curricular contents at school