Ubiquitous learning and project approach are genuinely connected. Project work has strong potential to provide both powerful contextual learning experiences and serendipitous exploration and discovery of the connected nature of information in the real world. Such promising features could equally be seen as challenges. More specifically, teachers struggle with technology resources’ accessibility and skills, lack of predictability in students learning endeavors, pressure of content-driven and standard-based instruction, mono-disciplinary curriculum and de-contextualized learning tradition, time as a limited resource, high stake testing and poor collaboration among teachers.