Transitioning from a linear economy to a circular economy (CE) in healthcare is essential for reducing human-induced environmental impacts and promoting sustainability. However, this shift is challenged by a lack of standardization in circular procedures. This article identifies key elements and challenges to implementing CE in complex industrial environments, with the use case of medical systems. These entail complex devices, such as Magnetic Resonance Imaging systems or Computed Tomography scanners. While CE principles have emerged in the medical industry, they must be improved and optimized especially in repair, maintenance and reuse processes, to support the decarbonization of healthcare. In the industrial case study, this is illustrated by the implementation of opportunistic maintenance for a spare part supply chain, or the use of a PSS-like (product-service system) model. In this context, literature is studied by focusing on three axes: (1) academic articles, (2) sustainability standards and frameworks for industrials, and (3) grey literature in a healthcare case study. This article aims to answer the following question: What are the main identifiable challenges to a circular economy in the medical system value chain, looking at a complex industrial environment case study? To better implement and evaluate CE in an industrial setting, companies need to reevaluate their business models and follow the 4.0 digital technology wave by augmenting or redesigning their ecosystems, facilitating the computation of circularity indicators. These metrics could provide more visibility and traceability on material flows, notably open & closed loop recycling, product returns, waste management and packaging loops. Additional constraints to achieve CE can be pinpointed by studying existing sustainability standards and policies on European or international levels. The results of the research identify twelve leading questions tackling CE reporting and evaluation, the digitalization of industrial ecosystems, and the identification of the initial steps to develop a Circular Digital Cockpit (CDC). Hence, four research themes are identified: (1) updating industrial paradigms for CE, (2) defining means for transitioning from LE to CE, (3) studying the status of CE in the healthcare industry, and (4) developing a CDC. The identified questions will guide ensued research and potentially discern gaps and hotspots for evaluating and monitoring CE practices, to ultimately create a comprehensive multi-faceted platform. Such a tool would bring decision aid to all steps in the medical device value chain, from product design to its end-of-life. Looking at the industrial use case, a preliminary framework to design this platform is proposed, with four structuring and interlinked pillars: robust data definition, circularity metrics, analytics & optimization, and models & simulation.