Effective self-management is the cornerstone of chronic disease self-management. However, self-management of chronic disease in patients with comorbid dementia is particularly challenging. It is vital that clinicians, patients and carers work collaboratively to tailor self-management programs to each patient with dementia. This study aimed to identify barriers and facilitators of successful self-management in the context of cognitive impairment in order to optimise the capacity for self-management for persons with dementia (PWD). A qualitative study based on semistructured interviews was conducted in Victoria, Australia. Interviews were conducted with 12 people (employed in the ambulatory and dementia care sectors), representing six health services. Participants identified a healthcare system that is complex, not dementia friendly and not accommodating the needs of PWD who have comorbidities. Individual and systemic barriers contributed to ineffective self-management. Chronic disease support programs do not routinely undertake cognitive assessment or have guidelines for modified management approaches for those with cognitive impairment. Support needs to be long-term and requires a specialised skillset that recognises not only chronic disease management, but also the effect of cognition on self-management. Although formal guidelines are needed, care also needs to be tailored to individual cognitive abilities and deficits.