Walking aids are widely used by older adults, however, alarmingly, their use has been linked to increased falls-risk, yet clinicians have no objective way of assessing user stability. This work aims to demonstrate the application of a novel methodology to investigate how the type of walking task, the amount of body weight supported by the device (i.e., device loading), and task performance strategy affect stability of rollator users. In this context, ten users performed six walking tasks with an instrumented rollator. The combined stability margin "SM" was calculated, which considers user and rollator as a combined system. A Friedman Test was used to investigate the effects of task on SM and a least-squares regression model was applied to investigate the relationship between device loading and SM. In addition, the effects of task performance strategy on SM were explored. As a result, it was found that: the minimum SM for straight line walking was higher than for more complex tasks (p<0.05); an increase in device loading was associated with an increase in SM (p<0.05); stepping up a kerb with at least 1 rollator wheel in ground contact at all times resulted in higher SM than lifting all four wheels simultaneously. Hence, we conclude that training should not be limited to straight line walking but should include various everyday tasks. Within person, SM informs on which tasks need practicing, and which strategy facilitates stability, thereby enabling person-specific guidance/training. The relevance of this work lies in an increase in walking aid users, and the costs arising from fall-related injuries.