Background Older adults with chronic illnesses or dependency on care who strive to age in place need support and care depending on their illness. Digital technology has enabled the possibility of supporting older adults in their wishes to age in place. However, current studies have mainly focused on the solitary evaluation of individual technologies or on evaluating technologies for specific illnesses. Objective This study aimed to synthesize research on the experiences of older people from the Western culture with chronic illnesses or care needs and their families with digital technology for aging in place. From the meta-synthesis, a model was derived that can be useful for the development of assistive devices in old age and that can support health care providers and professionals in their work with affected individuals. Methods A systematic review and qualitative meta-synthesis was performed using an inductive approach, as proposed by Sandelowski and Barroso. We performed a systematic literature search in 6 databases from 2000 to 2019, with an update in 2021 and, in addition, conducted a hand search in 2 databases, relevant journals, and reference lists. The results of each study were analyzed using initial and axial coding, followed by theoretical coding. A conceptual model was derived. Results A total of 7776 articles were identified. Articles were screened independently by 2 authors based on the eligibility criteria. Finally, of the 7776 studies, 18 (0.23%) were included in the meta-synthesis. The derived conceptual model describes older adults with chronic illnesses or dependency on care and their family members in an individual process of reflection and decision-making, starting with the use of a digital device. Older adults live in times of change. They experience stable and unstable times of illness as they are part of a changing digital world. Hence, older adults and their families consider digital technology a solution to their current situation. As they become familiar with a specific digital technology, they refine their needs and demands, gain confidence in its use, and note its advantages and disadvantages. They weigh hopes, needs, demands, and experiences in a process of reflection to decide on convenience and inconvenience. Independent of their decision, they achieve peace of mind either with or without digital technology. This process can restart repeatedly during the illness trajectory of older adults. Conclusions This study promotes a differentiated understanding of older adults’ experiences with digital technology. The conceptual model can be useful for the development of assistive technology in old age. Moreover, it can guide health care professionals in their work with older adults and their families to provide individual counseling to find the appropriate digital technology for their respective situations.