Privatization of transportation infrastructure is often accomplished through concessions contracts whereby the public agency transfers the costs of construction and/or operation and maintenance of the asset to the private entity for a period of time and in return, authorizes the private entity to then charge a user fee. Although this type of arrangement is not typical in the U.S, it is more common in Latin America and some European countries for large transportation infrastructure development and management. In the private sector, forensic engineers are commonly retained by stakeholders (owners, constructors, insurers) to investigate facilities that fail or do not perform as intended. Forensic engineers are often asked to determine the cause of a failure, identify the factors leading to a loss, assess risk, and assist in mitigation. Facilities constructed and operated under concessions create unique and challenging circumstances for forensic engineering investigations, as the contractual and risk allocation is different from traditional construction arrangements. This paper presents the unique challenges encountered by the authors for a forensic investigation of a construction defect claim made by a private consortium administering a tolled highway in Santiago, Chile that involved investors and insurance stakeholders from the U.S. and Europe. The construction and operation arrangements discussed in this paper will be of benefit to parties involved in management of public-private transportation facilities.