We consider identification of early warning signs (EWS) in projects. Project professionals are not good at detecting or acting on EWS. Barriers that lead to this are identified. The nature of EWS and their detection change with the evolving situation. Project assessments, typically part of gateways, are useful in identifying EWS connected to the formalities of the project. As complexity increases, assessments have more limited use, and the project is increasingly dependent on detecting EWS by informal “gut feeling.” Thus, knowledge, experience, and communication skills are increasingly important in complex situations. We conclude with a list of early warning signs.