The paper draws on two cases of learning settings that were converted to meet up-to-date educational requirements within these learning contexts. The authors address the role of stakeholder perspectives. Focusing on the learning situation, they present an articulation tool to aid dialogue between key stakeholder perspectives in a (re)design process. Dialogue is a way to figure out relevant issues and to establish the common ground between participants. The goal of a redesign process is that user requirements are well understood, and the design is embedded into local practices, informed of constraints and aware of potential opportunities regarding educational technology.