The call for the integration of program evaluation into the development of computer-supported learning environments is ever increasing. Pushed not only by demands from policy makers and grant givers for more accountability within lean times, this trend is due also to the fact that outcomes of computer-supported learning environment projects often fall short of the expectations held by the project teams. The discrepancy between the targets set by the project staff and the outcomes achieved suggests there is a need for formative evaluation approaches (versus summative approaches) that facilitate the elicitation of information that can be used to improve a program while it is in its development stage (c.p., Worthen, Sanders & Fitzpatrick, 1997). While the call for formative evaluation as an integral part of projects that aim to develop complex socio-technical systems is widely accepted, we note a lack of theoretical frameworks that reflect the particularities of these kind of systems and the ways they evolve (c.p., Keil-Slawik, 1999). This is of crucial importance, as formative evaluation will only be an accepted and effective part of a project if it provides information useful for the project staff. Below we outline the obstacles evaluation faces with regard to projects that design computer-supported learning environments, and discuss two promising approaches that can be used in complimentary fashion.