The aim of this paper is to develop an approach that can be used in addressing the issue of the use of information technology and its importance in human meaning making. By using a combination of Wittgenstein's work method, a sociocultural perspective on learning, and a sociotechnical perspective on artifacts a specific focus for analyses was discerned: the relation between the use-of-technology in meaning-making on one hand and the circumstances for this meaning-making on the other hand. The conversations of six groups of children, who worked with an assignment, that required that they doubted information they encountered, were video recorded and analyzed. The analyses were done in three interrelated steps. (a) The students use-of-technology in meaning making, (b) the meaning patterns that the students encounter on the web, and (c) students' intentions and habits. Our findings show that, while the mode of reinforcement of the texts used by the students may have provided little opportunity for doubt or learning how to doubt, the students' habits and intentions with their work determined the result of the interaction, namely copying information from the web. Taking our point of departure in this empirical illustration we discuss theoretical and methodological questions concerning the understanding of the use of information technology in educational settings.