It’s hard to argue against the concepts of self-describing data, contextual interfaces, and richer metadata for content that eventually will make up the Semantic Web. The need is just so great, and becomes greater by the day with the huge increase in unstructured content and non-integrated data repositories. However, it is easy to imagine semantic environments suffering from the same challenges that many content management system implementations and the Web itself suffer from: the preoccupation with publishing and storing metadata could easily leave us drowning in it. If there’s one thing that “six degrees of separation” shows us, it is that everything can be related to everything else. Will we evolve meaning in a mass of loosely assembled associations? This paper focuses on the authors’ maintenance design challenges, and the approaches being explored to promote feedback and user involvement for the maintenance of semantic representations, to ensure they remain useful and cu...