Mobile and wearable technologies offer the promise of great opportunity, connection, new experiences, and natural interactions. However, what happens when these designs do not fully consider the relationship between people and the devices they use? For example, wheelchair users often use and carry multiple mobile computing devices, such as laptops, tablets, and smartphones. Upper body motor impairments or physically restrictive wheelchair frames may limit wheelchair users’ ability to interact with these devices. Designing technology for wheelchair users requires constant negotiation between the user’s needs, technological and functional constraints, and the context in which the technology is used. My research aims to support a broad range of people with diverse abilities as they interact with the world and people around them. I use Chairables to conceptualize the design approach that leverages the affordances of wheelchairs for mobile interaction. Our ongoing research aims to support and empower people with disabilities as they engage in a range of activities, including online social interactions, competitive sports, and mobility.