This chapter attempts to contribute toward exploring fundamental conceptualization on collaboration and pervasiveness in education. An assigned task is to clarify my concepts on collaborative learning based on ubiquitous computation and Semantic Web perspectives by means of more originated ways. Collaborative activities and computer-supported collaborative learning (CSCL) per se consists of various needs to encourage motivation and understandings of each student in more effective learning style and environment. We can recognize that collaborative learning in a ubiquitous environment can provide more interactive, experiential, spatiotemporal, and distributed aspects for anyone who wants to know information and solve educational tasks coordinating with others at any time. Then, I would like to show my design of the ubiquitous jigsaw method and self-organizing networks in the learning community. Further, I concentrate on exploring possibilities of collaborative learning with semantic technologies which allows to inspire and facilitate a more reciprocal exchange among affiliated relationships in a ubiquitous environment. Finally, I will discuss these topics.