Due to the high effort to implement Computer Supported Cooperative Work (CSCW) in education, the institutions concerned react cautiously to new requirements of future engineers, e.g. Software Engineering. The CSCW and Software Engineering lab at University of Duisburg-Essen (UDE) is conducted as a project setup of students’ teams, each team consisting of four persons spatially distributed. This article describes the efforts that have been made at UDE concerning the development of new education methodology in a distributed collaborative environment. In the context of distributed collaborative learning, it is usually difficult for students to be aware of others’ activities and for instructors to oversee the process and regulate the collaboration. In order to facilitate collaborative learning, intelligent agents were developed to support the awareness and regulation of the collaboration. This article discusses the roles of intelligent agents and how they support students and instructors in a synchronically distributed collaborative-learning environment: PASSENGER. Furthermore, multicultural differences between the learners is an important issue which can influence learners’ collaboration processes (such as participation, coordination, teacher intervention, or group interaction) in a distributed collaborative learning environment where users are geographically distributed and collaborate through a web-based learning environment. This article also highlights the cultural awareness dimension of intercultural communication amongst geographically distributed learners.