While collaborative contracting methods have been successfully tested and implemented in construction projects in many countries and over several decades, it has proved difficult to sustain long-term learning in this field. Collaboration has frequently been promoted as a panacea for various problems, where high performance goals have been followed by disappointments and, subsequently, by contrary policies that prohibit collaboration. Such pendulum movements suggest that industry actors fail to appreciate the full complexity involved when introducing novel contracting methods more broadly in the construction sector. A fundamental aspect is that less visible factors at the industry and organizational levels underlie the obstacles and relational problems that play out at the project level. The purpose of this chapter, therefore, is to identify and discuss key barriers to collaboration at all levels, how they interact and how sector-level learning can be improved.