Workers commodifying their time in labour markets are liable to become temporarily incapable of doing so because of sickness or caregiving responsibilities. While the risk is universal, it will be experienced very differently depending on social conditions and arrangements and social locations, such as gender, among others. In a society in which the vast majority of people are dependent on labour market incomes to survive, the consequences of being off work are severe, unless some protection and benefits are provided. Over time, Canada has developed a number leave and income-replacement schemes, but the COVID-19 pandemic revealed, in dramatic fashion, their limitations, leading to the adoption of temporary measures to address the crisis. This article, written from a feminist political economy perspective, provides an overview of the historical development of sickness and caregiving leave and pay arrangements set against the background of changing social and economic reproduction regimes. It then examines more closely the slow development of Canada’s welfare state model of sickness and caregiving leaves and benefits since the 1970s, focusing on the federal government’s enactment of special employment insurance benefits and statutory leave rights in British Columbia and Ontario. Next, it critically examines the limitations of that statutory regime, as it existed immediately prior to the outbreak of the COVID-19 pandemic in Canada, and then considers the expansion of sick and caregiving leave and pay provisions, enacted in response to the pandemic. The article then elaborates four principles to guide the future development of the sick and caregiving entitlements suggests ways of bringing the existing regime more into line with those principles. Finally, it sets out a few directions towards imagining a different regime that truly provides workers with what we conceive they are owed as a matter of common humanity.