Older people living alone (OPLA) are considered vulnerable because of fewer resources, such as social support. As self-management becomes increasingly important in chronic care, evidence is needed on how to better support OPLA. This review synthesizes the evidence from 32 publications on the challenges as well as strategies of OPLA in managing chronic conditions. On the basis of a systematic database search and review process, being independent and being at home were identified as crucial when living alone in later life; both involve decision making and the adjustment of routines to manage everyday life and chronic conditions. These findings show that OPLA are vulnerable because of difficult living situations, limited resources, or a lack of support, and they actively manage their conditions using various strategies to remain independent, but these may cause fragile arrangements that can jeopardize independence. Awareness of these strategies is a starting point to develop interventions for self-management support in chronic illness.