Taking medications as prescribed can be difficult, especially for older adults who often need to remember multiple doses. While technology and other interventions exist to help people and their caregivers with medication management, most of them are unreliable when dealing with complex medication regimens. Previous research shows that robots could provide reminders as well as social and emotional support, offering a promising alternative for assisting both older adults living independently and caregivers helping them manage complex medication regimens. In this paper, we explore how social robots could support homebased medication management. We present the results of 6 workshops conducted with 10 informal and 8 formal caregivers, and 10 interviews conducted with older adults to further understand their experiences and challenges with medication management and the potential role of robots to support them. We identify tensions between practical challenges of keeping robots in home settings (e.g., maintenance, cost) and their potential benefits supporting both older adults and caregivers (e.g., providing medication and emotional support, and monitoring patients). Based on our findings, we provide discuss several implications for the design of social robots that need to be taken into account before deploying robots in home settings.