Background: Family carers of older adults with disability often both experience stress that may affect their ability to provide care, and find some caregiving activities differentially challenging. Objectives: The objectives of this research are to identify the caregiving activities that are most problematic to carers and to explore the reasons why carers found these activities challenging. Methods: Participants were past or current carers aged 19 years and older. Using an explanatory sequential mixed-methods approach, data were collected through a survey and open-ended interviews. Findings: Thematic analysis revealed that an activity was likely to be more problematic if it had to be coordinated with other caregiving needs or where a care recipient's disability was severe.