Caregivers provide critical support for older adults managing multiple chronic conditions (MCCs), but few studies describe the assistance caregivers provide or identify factors influencing their provision of support. We conducted qualitative interviews with 25 caregivers to older adults with MCCs to describe caregivers’ roles and identify the factors that influence caregivers’ ability to carry out these roles. Transcripts were analyzed using the Framework Method. Caregivers supported the management of MCCs in several ways, including monitoring conditions, communicating with clinicians, and tracking health information. Disagreement, or conflicted relationships, between caregivers and older adults over health and behaviors influenced the provision of support, resulting in less involved and less effective caregivers. Caregivers in conflicted relationships were more challenged by resistance from older adults. Greater agreement, or collaboration, between caregivers and older adults resulted in more involved and effective caregivers. Addressing health-related conflict may enhance caregivers’ capacity to support older adults with MCCs.