Over the past 50 years, Kenya’s payments and banking systems have undergone both incremental and revolutionary modifications that have transformed Kenya’s financial landscape, from cash transactions to digital finance ecosystems. M-PESA, rolled out in 2007, undoubtedly has earned its place in Kenya’s Hall of Fame. The developments in the payments system have culminated in a more accessible, effective and efficient Kenyan payment system. This chapter tells the M-PESA story from the lens of a regulator, from conception to the eventual launch in March 2007. More importantly, the chapter tells other understated stories of payments and related banking sector innovations that have seen the level of financial inclusion in Kenya triple from 26 per cent in 2006 to over 75 per cent in 2016. The chapter provides lessons learnt in this transformational journey, one being the need for regulators to understand the business models underpinning innovations, risks thereon, and their mitigating factors.