This research aims to examine for whom combining work and family/caregiving may be most harmful. Employed parents, elder caregivers, and the sandwiched generation were compared with their coworkers without such responsibilities. Based on the job demands–resources model, we assumed that high job demands/low job resources would relate to work-to-family conflict (WFC) and low job demands/high job resources to work-to-family enrichment. However, this effect would depend on employees’ family/caregiving responsibilities. Using a large sample of Slovenian employees (N = 1,285), we found support for the moderating role of the type of caregiving responsibility between workload and WFC. In addition, the type of caregiving had a moderating effect on the relationship between coworker support and WFC. Support was also found for the differential impact of job resources on work-to-family enrichment. The results therefore indicate the relevance of types of caregiving responsibility in work–family research and practice.