This chapter uses the case studies to demonstrate the existing gap between the way decisions making is taken at the higher layers of an organization and how those decisions actually work on the job-site. The first case study concerns a Canadian oil and gas organization that ran heavily over budget while planning the development of its second rig in the Peruvian Amazon rainforest. The second case study describes comparable operational challenges in the Peruvian rainforest, though the focus in this case was the project's sustainability profile and the hazards the organization faced as a consequence of the way operations were managed. The role of indigenous communities in project sustainability, along with the challenge of complex environmental management, forms part of a series of topics that are intended to complement the first case study. The chapter contradicts good collaborative project enterprise lead (CPEL) and corporate social responsibility (CSR) practices when it comes to economic considerations like in the last case study.