This paper presents an organic view of prototyping for managing dynamic factors involved in evolutionary design of information systems (IS). Those dynamic factors can be caused by, for example, continuing suggestions from users, changes in the technologies, and users-designers learning related stepwise progresses. Expanding the evolutionary prototyping to ‘start small and grow’, the organic view of prototyping proposes two prerequisites to do so, namely 1) a sustainable and adaptive ‘embryo’ – an organic structure of the future system, and 2) an embedded learning and feedback management that the actors of the system (users, designers, decision makers, administrators) can communicate with each other. An example of eHealth system design demonstrates how the prerequisites can be implemented.