Addressing the subject of Case-Based Reasoning (CBR) in architectural design, we present a Web-based design assistant for student- and professional architects called DYNAMO. Its main objective is to initiate and nurture the life-long process of learning from (design) experience as suggested by CBRis cognitive model. Rather than adopting this model as such, DYNAMO extrapolates it beyond the individual by stimulating and intensifying several modes of interaction. One mode - the focus of this paper - concerns the interaction between the realm of design education and the world of practice. DYNAMO offers a platform for exchanging design efforts and insights, in the form of cases, between both parties, which perfectly chimes with the current tendency towards life-long learning and continuing education. Just like our university advises graduates to “Take a maintenance contract with your degreei, architecture schools may encourage recently qualified architects to subscribe to DYNAMO. To what extent the tool can fulfill this role of maintenance contract is discussed at the end of the paper, which reports on how DYNAMO was used and appreciated by professional architects at different levels of expertise.