Digital technologies play a central role in strategies to improve access, quality and efficiency of health care and services. However, many digital health projects have failed to become sustainable and spread across health organizations and systems. This situation is partly due to the fact that these projects are often developed and evaluated by reducing the issues linked mainly to the technological dimension. Such tradition has paid little attention to the fact that technology is introduced into pluralistic and complex sociotechnical systems such as health organizations and systems. The aim of this article is to propose practical and theorical, non-prescriptive, elements of reflection that can serve as a basis for evaluating complex and innovative digital health projects. This reflection builds on the lessons learned from the application of a strategic framework for evaluating three major complex and innovative digital health projects in Quebec over the last 15 years.