There have been significant changes in the health insurance industry in India since four decades when it emerged as a small, government-run scheme which has now become a competitive and thriving industry, contributing significantly to the nation's health financing. The paper attempts to trace the evolution of mediclaim insurance in India and highlight the major notches as they developed and underline how the market evolved and how regulatory changes have been the driving factors in shaping the industry. It is a review of the potential which has emerged from rising health consciousness, demographic changes, advances in technology, and policy measures attempting to expand access to insurance. At the same time, the study also shines the spotlight on continuing challenges such as low insurance penetration, high expenditure on out-of-pocket healthcare, low efficiencies and low awareness in rural as well as among the poor. Using a qualitative and analytic framework, this manuscript is based upon the review of literature, market reports and policy documents to provide an understanding of the changing landscape of mediclaim insurance in the healthcare landscape in India. Results imply that although substantial progress in diversity of products and providing service through digital source had contributed to non-regressive market growth, factors stemming from the system level held back equitable growth of health insurance across different levels of socio-economic status and above. The paper ends with strategic perspectives and policy recommendations for the policy makers, highlighting importance of sustainable and inclusive policy frameworks, consumer education, innovative insurance product designs and inclusion of digital health technologies to provide for wider access, affordability and financial serenity to the Indian masses.