The chapter introduces a novel financial arrangement in healthcare services: Health Impact Bonds (HIBs). Transition aims at making healthcare services not only more affordable but also more efficient, the reason why HIBs focus on the performance (output) side of services (pay-for-success contract). The chapter describes the urgency and challenges in moving towards illness prevention, on the system (healthcare) and project levels. Next, it is explored how HIBs can improve situations of care investment that does not (fully) precipitate at the investor while preventing the rise of new problematic situations. Accordingly, a preliminary list of conditions is designed for the alignment of HIBs. Overall, it seems that HIBs provide substantial solutions by combining new contracts on paying-for-success in performance and a shared savings contract, although some questions remain regarding the involvement of investors. The concluding section includes a reflection on city involvement in HIBs.