Objective: The modern-age digital healthcare system empowers the healthcare professionals and patients to effectively monitor and manage chronic disease conditions remotely and offers significant benefits such as improved patient outcomes, clinical decision support, and reduced HCP’s workload. The digital healthcare system includes connected medical devices, organisation infrastructure, hospital networks, mobile apps, and multiple stakeholders such as device manufacturers, HCPs and patients. The key elements of a digital healthcare system include interoperability and cybersecurity. The interoperability ensures integration of medical devices, electronic health records (EHRs) and other systems for seamless data exchange. Whereas the cybersecurity ensures systems are resilient to minimise the threats and vulnerabilities for patient data security and privacy. The objective of this research is to evaluate the roles of interoperability and cybersecurity through the assessment of enablers, drivers, and barriers, respectively, in remote patient monitoring medical devices of chronic disease management by exploring the knowledge of different stakeholders involved in the development and application of similar systems. Methods: A qualitative exploration of information gathered through interviewing experienced stakeholders such as healthcare professionals, research and development engineers, regulatory affairs specialists, medical affairs professionals, marketing professionals and cybersecurity professionals involved in the development, and application of remote patient monitoring medical devices of chronic disease management. The interviews were focused on gathering experience and insights on interoperability and cybersecurity. Results: Consensus across participants on benefits such as improved patient outcomes and clinical decision support. The current state of interoperability framework and features facilitate data exchange leveraging existing standards. However, significant efforts were required to develop standardised communication protocols and open architecture for integration of entire digital healthcare system. The current state of cybersecurity framework and regulations such as GDPR and HIPAA ensure data protection. However, more efforts are required to improve the system resilience and data security, by following approaches such as “security by design”, role-based access and enhanced authentications. Conclusion: The insights shared by the participants resemble with the literature review findings. The RPMDs offer significant benefits if implemented effectively to improve patient outcomes and support clinical decisions. The development and implementation of efficient RPMDs require standardised communication protocols, scalable framework, open architectures and specific standards to integrate devices in a network securely and exchange data seamlessly for effective interoperability, and with enhanced cybersecurity measures to protect patient data.