Despite the potential benefits of powered mobility, many older adults do not have access to this technology. To date, few studies have explored how prescribers make decisions regarding provision of powered mobility. Therefore, we undertook a qualitative study to develop a better understanding of prescribers’ attitudes toward and practices with older adult candidates for powered mobility devices. Our analysis of 10 in-depth interviews identified three main themes: (1) “Deciding who should be entitled” explored how therapists decided who should have access to powered mobility, (2) “power wheelchair negotiation” described the discord between clients and therapists that became apparent during this process, and (3) “practical considerations” revealed how contextual factors shaped the provision of powered mobility. The findings suggest that the ways in which powered mobility is funded, provided, and accommodated should be improved so that more older adults have access to these devices and can use them to their full potential.