This paper report several related failures of modeling interventions. Atrivé, an organizational consulting company, set out to adapt the canonical housing association model, named ITS, (Vennix, 1996) for the specific circumstances of its clients. The ITS adaptation process, however demonstrated rather annoying dynamics and had finally to be terminated due to negative business results. This paper provides a background on the relevance of failure case studies and ventures into the symptoms and warning signs. We reflect on a system thinking intervention within the company to learn from these experiences and improve business strategy and project the problems encountered onto the core set of archetypes. We conclude by summarizing several known and one possibly new factor in modeling failure and pose several questions for further research.