An increasing number of adults, both men and women, are simultaneously managing work and family caregiving roles. Guided by the stress process model, we investigate whether 823 employees occupying diverse family caregiving roles (child caregiving only, elder caregiving only, and both child caregiving and elder caregiving, or “sandwiched” caregiving) and their noncaregiving counterparts in the information technology division of a white-collar organization differ on several indicators of psychosocial stress along with gender differences in stress exposure. Compared with noncaregivers, child caregivers reported more perceived stress and partner strain whereas elder caregivers reported greater perceived stress and psychological distress. With the exception of work-to-family conflict, sandwiched caregivers reported poorer overall psychosocial functioning. Additionally, sandwiched women reported more family-to-work conflict and less partner support than their male counterparts. Further research on the implications of combining a white-collar employment role with different family caregiving roles is warranted.