Work-based learning often suffers from lack of opportunities and space for learning activities as part of everyday work processes. One possibility is the active involvement into collective sense-making processes, e.g., how to translate new or updated clinical guidelines into changes of processes and treatment at a concrete practice. This active involvement requires sharing of opinions, ideas, and other “immature” pieces of information/knowledge. However, a major obstacle lies in individuals’ reluctance to share and use immature knowledge if they experience uncertainty about the maturity. Living Documents tries to address this issue. It is a web-based system that allows for collaboration and knowledge development based on the metaphor of a living document. Such living documents combines stable and more mature parts with emergent comments and opinions, which are made first class citizens. Document, sub-documents, and comments can be associated with knowledge maturing indicators. In this respect, the approach to support learning has been based on the knowledge maturing model. The system promotes knowledge maturing by providing a contextual space for conversations that can be linked to more mature knowledge.