This chapter presents a set of requirements for next generation groupware systems to improve team cooperation and awareness in distance learning settings. The premise of the chapter is based on the observation that in distance learning online asynchronous (e.g., e-mail, conference tools) or synchronous (e.g., chat) mechanisms are used to facilitate collaboration and coordination to complete necessary tasks. However, students are neither trained in basic principles regarding how effective cooperation takes place, nor means for their realization. Basic methods of cooperation are delineated along with a set of requirements based on a critical analysis of the elements of cooperation and team awareness. The means for realizing these elements are also discussed to present strategies to develop the proposed elements. Two scenarios are examined to demonstrate the utility of collaboration to provide deep integration of communication and task accomplishment within a unified coherent framework.