In 2012, the government of Colombia enacted Law 1508, providing new regulations for public-private partnerships (PPPs), and initiated a new generation of road concessions. Under this framework, control instruments are based on operational performance indicators, and revenues for the private party become available only when the infrastructure becomes fully functional and complies with service metrics. Risks associated with operation phases are now significant in contrast with conventional risk analyses that prioritize the construction phase. Although the construction period is shorter than the operation period of PPP projects, very little analysis is available for operational risks. This study proposes a qualitative research and case study methodology, with the comparison of road concession cases in Spain and Chile with Colombia, and the analysis of contractual documents and performance reports as a source of operational performance requirements, risk allocation, and activation events. Nonconventional factors are identified, such as third-party influence and user behavior, opposite motivations in demand management between toll income and maintenance requirements, negative incentives in availability payments, split incentives in the public-private relationship, and ambiguous definition in force majeure events and insurance coverage. Recommendations are proposed for further risk assessment and allocation.