This chapter covers the evolution of the microinsurance regulation of Insurance Regulatory and Development Authority of India (IRDAI) and the corresponding journey of the microinsurance sector in India. The Regulation of Social and Rural Obligation 2002 and the Microinsurance Regulation of 2005 kickstarted a series of initiatives by insurance companies that were eager to collaborate with Non-Governmental Organizations (NGOs)/Microfinance Institutions (MFIs) to cover the space. Annapurna Pariwar (AP) faced challenges in these collaborations and started its sole journey of setting up mutual insurance to cover the health risks of its members. The chapter examines the position and contribution of Annapurna in offering risk management solutions and the challenges faced in this regulatory space. It also discusses how mutual insurance is placed in the current guidelines and its impact on organisations like Annapurna. It discusses other regulations like Point of Salespersons, IMF Regulation, and CPSC Regulation, which were intended to increase access to insurance for the masses. It touches upon the initiatives taken by the regulator to make insurance more inclusive for smaller organisations that are providing innovative alternatives to the low-income segment of society. It concludes with recommendations that will help AP upscale and handhold other community-based organisations in offering insurance. These changes will be important in achieving the ‘Insurance for All by 2047’ targets set by IRDAI.