In this article we propose that the grammar of schooling [Tyack, D., & Tobin, W. (1994). "The 'grammar' of schooling: Why has it been so hard to change?" "American Educational Research Journal, 31"(3), 453-479.] is responsible not only for the well-known and world-wide difficulties in integrating ICT into formal educational settings, but also for the replication of traditional models when this integration occurs. In clear contrast with this domain, in out-of-school projects ICT is integrated in innovative and truly "disruptive" [Blin, F., & Munro, M. (2008). "Why hasn't technology disrupted academics' teaching practices. Understanding resistance to change through the lens of activity theory." "Computers and Education, 50"(2), 475-490.] ways. To exemplify this integration, we have selected and described two successful, although different in nature, out-of-school projects. The first one, "Pincel y Raton," seeks to develop creativity in children and to educate them to use ICT in a reflexive and useful manner. The second project, "Menosca," pursues children's understanding of their historical and social environment through the use of GPSs, digital photography and web-page design. Both experiences underscore the multiple and varied possibilities that ICT affords for meaningful learning when the constraints inherent to the school setting do not seem to apply. By contrasting the formal and the out-of-school experiences, it is possible to unveil and bring to consciousness the principles and rules of the "grammar of schooling." We propose that becoming aware of the features of this grammar, i.e., philosophy, course design, time and place, tasks, resources, outcomes and products and assessment, is the first step toward change.