As workers struggle to combine work and family responsibilities, discrimination against workers based on their status as caregivers is on the rise. Although both women and men feel the pinch, caregiver discrimination is particularly damaging for women, because care is intricately tied to gendered norms and expectations. Drawing on a sample of caregiver discrimination cases resolved by Canadian Human Rights Tribunals from 1985 through 2016, I will discuss the clash between work and care and how gendered expectations about work–life facilitation inform legal disputes over caregiving and their outcomes. Through analysis of case issues and outcomes, I will show that although women are more likely to bring claims and obtain favorable outcomes, the legal interpretation of claims is highly gendered. Women bring claims involving both their presumed status as caregivers and the practical challenges of seeking accommodations for care, whereas men’s claims are largely about accommodations. In adjudicating cases, Tribunals are more likely to see women as lacking credibility when making their claims, questioning their competence and legitimacy, while men struggle to convey how seriously work interferes with family responsibilities. I will discuss the implications of these findings for workers’ capacities to do their jobs and care for their families during the Covid-19 crisis and beyond.