Individuals with multimorbidity commonly have several concurrent prescriptions and experience healthcare obstacles related to managing different diagnoses and medications. This study aimed to provide a deeper understanding of how older adults with multimorbidity experience medication self-management and how this is affected by the healthcare system. The National Board of Research Ethics approved the study, and 20 older adults with multimorbidity participated in in-depth interviews that were analysed using a hermeneutic approach. Three levels of interpretation emerged. At the first level, lack of participation in healthcare communication hinders adherence and safety, and feeling abandoned to self-care leads to health risk-taking. At the second level, the healthcare organisation is seen as an obstacle to medication self-management. The overall interpretation was a system of repairing ‘parts’ but not enabling the experience of health. This study shows that the healthcare system is able to treat and relieve an individual's symptoms, but seems unable to help them achieve and promote good health, or to provide the support they need to function in everyday life.