From 2005 to 2008 the international research and development project iCamp carried out a series of targeted educational interventions into existing teaching and studying practices within a cluster of European universities. These interventions were meant to establish educational experiences that would correspond with key features of international, distributed and technologically mediated work settings. The main educational objective was the advancement of important dispositions (skills, knowledge, attitudes and orientations) for collaborating with others and for self-directing intentional learning projects in such settings. The large-scale, homogenous and centrally administered landscapes of tools and services commonly provided in institutions of higher education proved to be conceptually and technologically incompatible with iCamp's overall intervention perspective. Instead, iCamp fostered the systematic use of loosely-coupled, networked tools and services in the realm of social media and social software (such as Wikis, Weblogs, Webfeeds, etc.) to augment personal and distributed learning environments. The conceptual and technological shift provoked by iCamp challenged institutional representatives, facilitators, and students alike. This paper focuses on the description and interpretation of some key challenges, tensions, and barriers experienced by the research and intervention team in the context of the final field study carried out within the project. The paper finally suggests that the reported challenges and barriers represent re-occurring problems in educational research and argues for the need to develop an adequate conceptual framework for educational intervention that focuses on second-order change.