Background and Objectives Although sleep is a critical health outcome providing insight into overall health, well-being, and role functioning, little is known about the sleep consequences of simultaneously occupying paid and unpaid caregiving roles. This study investigated the frequency with which women employed in U.S.-based nursing homes entered and exited unpaid caregiving roles for children (double-duty-child caregivers), adults (double-duty-elder caregivers), or both (triple-duty caregivers), as well as examined how combinations of and changes in these caregiving roles related to cross-sectional and longitudinal sleep patterns. Research Design and Methods The sample comprised 1,135 women long-term care employees who participated in the baseline wave of the Work, Family, and Health Study and were assessed at three follow-up time points (6-, 12-, and 18-months). Sleep was assessed with items primarily adapted from the Pittsburgh Sleep Quality Index and wrist actigraphic recordings. Multilevel models with data nested within persons were applied. Results Women long-term care employees entered and exited the unpaid elder caregiving role most frequently. At baseline, double-duty-child and triple-duty caregivers reported shorter sleep quantity and poorer sleep quality than their counterparts without unpaid caregiving roles, or workplace-only caregivers. Double-duty-elder caregivers also reported shorter sleep duration compared to workplace-only caregivers. Over time, double-duty-elder caregiving role entry was associated with negative changes in subjective sleep quantity and quality. Discussion and Implications Simultaneously occupying paid and unpaid caregiving roles has negative implications for subjective sleep characteristics. These results call for further research to advance understanding of double-and-triple-duty caregivers' sleep health and facilitate targeted intervention development.