Transport is an important arbiter of engagement in society. Disability and functional limitations (cognitive and physical) associated with older age can make such participation challenging. The design and engineering community have been strident in recent decades to use technology to mitigate, as far as possible, the limitations imposed upon individuals as a consequence of the effects of ageing. This chapter explores one such assistive technology; the motorised mobility scooter (MMS) and in particular examines some contradictions and ambiguities associated with this increasingly popular form of mobility. For example, MMS are classified as pedestrians yet can travel at speeds of 10 km/h. They can look and perform similar to bigger motor scooters but are not permitted to travel in traffic lanes. These issues have significant implications upon the safety of the user and other pedestrians. From a review of the scientific literature and examination of injury data from the Australian experience, some implications are drawn for systems-based strategies engaging design, policy and regulation approaches to enhance the safety of this form of assistive technology. These approaches have potential benefits that may extent to other parts of the world where this form of mobility is also growing in popularity.