The emergence of new skills to better fit the networked information economy presses higher education institutions to invest in digitally rich environments that allow learning to be personalized, taking place in multiple locations and at time that suits the learner. Social Web tools prioritize collaboration, participation, and reflection, offer new opportunities for knowledge construction and sharing, but they also demand new pedagogical strategies and assessment methods that are not consistent with standards that value what is taught instead of what is constructed, what is pre-established instead of what is democratically agreed. In this chapter, the author presents the results of a research project where different Web 2.0 technologies were used as tools for assessing learning in teacher education programs at the University of Minho, Braga, Portugal between 2006 and 2012. In order to provide rationale for embracing Web 2.0 tools as well as recommend alternative methods to create, capture, and assess learning outcomes that result from the integration of authoring tools in teaching and learning activities, the authors discuss the evidence obtained and reflect on the affordances and challenges of setting up authentic tasks that engage students in the learning process and that provide inferences to assess learning outcomes.