This paper presents the findings from four case studies on stakeholder engagement in new health information and communication technology (ICT) product-service system (PSS) development. The degree of connectivity between the new health ICT PSS and its operating environment has emerged to be an important contextual factor that may impact stakeholder engagement in the early stage development process. Along with the proposition of a four-level framework to guide systematic stakeholder identification for new PSS development, three other propositions for analyzing stakeholder engagement based on the degree of connectivity are developed. Analysis of the findings has shown that the connectivity between an ICT PSS and its operating environment can be separated into data connectivity and process connectivity. Moreover, each type of connectivity could be characterized in terms of three categories: independent, linked or incorporated. Furthermore, depending upon whether and to what extent the PSS has data and process connectivity with its intended operating environment, the stakeholder engagement needs in early stage development vary. The propositions presented in this paper provide important directions for future work exploring how contextual factors impact stakeholder engagement in early stage new PSS development in the healthcare industry.