The use of mobility devices, such as walking sticks and rollators, increases during the ageing process. Our aim was to explore how very old single-living Swedish women experience the use of mobility devices over time, in relation to everyday occupation. A multiple case study strategy involving quantitative and qualitative data was used. The findings indicate that the use of mobility devices, rollators in particular, starts off as support for walking but over time becomes more involved in occupational performance, resulting in complex transactions between personal, environmental, and task components. Personal factors such as ability to adjust and adapt to different situations seem to be crucial for optimal mobility device use. Strategies and adaptive behavior were developed over the years while striving for maintained independence and participation. The use of mobility devices was described as something one has to accept, but also a constant reminder of your limitations, or as a possibility to remain active and to manage everyday occupation. The findings stress the need to adopt a comprehensive view when trying to facilitate everyday occupations in very old age. Physical, social, psychological aspects, combinations among assistive devices, and home modification all need to be reflected on and monitored over time.