Family-to-work stereotype threat (FWST) occurs when employees fear confirming negative stereotypes about workers with caregiving responsibilities. Although a substantial proportion of workers in the U.S. and Italy have caregiving responsibilities (e.g., child or elder care), there is relatively little research on how family-to-work conflict (FWC) may impact employee safety outcomes, nor the mediating and moderating mechanisms involved in explaining these relationships. The current study tests cognitive failures as an explanatory mechanism for the relationship between FWC and workplace accidents and injuries. Additionally, we also test whether employees who experience higher levels of FWST are more vulnerable to adverse safety-related outcomes as a result of FWC. Using lagged data from a sample of N = 196 U.S. employees and cross-sectional data from a sample of N = 814 individuals nested within n = 100 organizations in Italy, results indicate that greater FWC and higher FWST are both related to increased work-related cognitive failures; such cognitive failures are related to more experienced accidents and injuries at work. Notably, within the U.S., these relationships are significantly exacerbated among employees who fear they are confirming negative stereotypes about employees with family obligations. Within Italy, this interaction was only observed among employees of private companies. We discuss our findings in light of the increased blurring of work and life boundaries, and possible legislative and cultural variables explaining differences between the two countries.