Ever since their beginning in 1986, Healthy Cities projects all over the world have been confronted with the issue of evaluation. However, after 20 years, many key dilemmas constantly reappear, people often looking for a kind of 'magic' list of universally applicable indicators to evaluate these initiatives. In this article we address five questions, allowing to illustrate the evaluative dilemmas the Healthy Communities movement is confronted with: Why evaluate Healthy Cities? What should be evaluated? Evaluate for who? Who should undertake the evaluation? How should the evaluation be performed? We conclude by formulating three recommendations in order to stimulate exchanges and debate. Our argument is based on a recent thorough analysis of the evaluative literature pertaining to the Healthy Cities movement, as well as on two decades of reflection on and involvement with this issue locally, nationally and internationally.