Ubiquitous Learning is an emerging field that deeply relies on the Ubiquitous Computing paradigm reflecting the pervasive presence of computers in everyday living. In these days of technology reshaping almost everything, it is quite difficult to escape awareness that new forms of living have already arrived. Thereby, this new way of living is also promoting new learning scenarios where handheld devices allow our students to be connected anytime-anywhere. Ubiquity in time and place also brings ubiquity in expectation and interpretation. However broad the scatter, ubiquitous technology by itself does not guarantee that practical and scholastic learning will take place in those scenarios. A step forward is needed to reflect formally and informally upon current Ubiquitous Learning practices. Educators, developers and curriculum designers should work together in the processes of designing, enacting and evaluating Ubiquitous Learning Environments (ULE). They should become more aware of whether or not a ULE is actually promoting new learning/teaching practices (and perhaps impeding old ones). This is a formidable challenge since much of Ubiquitous Learning is hidden from view, not prominent in experience, and requires special excavating to find. Ubiquitous Learning necessitates constant innovation due to the incessant growth of new Instructional Computerized Tools. Standard approaches to formal evaluation have difficulty in dynamic, non-summative situations where practitioners play never-ending active and creative roles. To cope with this situation we address the perceived need to adapt and extend traditional evaluation models to these new circumstances. Notably, we will take into account some relevant issues within the UL field such as the increasingly elastic boundaries of Education, emerging agency issues, the serious recognition of learner differences, and the mix of representational modes of our mediated society. A more responsive and situated approach to evaluation seems to us the strategy to better illuminate the shadowed sides of UL.