A plethora of assistive technologies are designed to cater to relatively common types of disabilities. However, some people have disabilities or circumstances that fall outside these pluralities, requiring a bespoke assistive technology to be developed and custom built to meet their unique requirements. To explore the opportunities and challenges of such an endeavor, we document the process undertaken to build a braille keyboard for a one-handed blind person over the course of 18-months. This process involved iterative prototyping within an intensive co-creation process, due to the unique needs arising from having two intersecting impairments and the challenges of efectively developing an entirely new format of AAT. Through a structured refection on this process, we provide an account of the practical, pragmatic and ethical considerations that apply when developing a bespoke assistive technology, whilst illustrating the wider value of bespoke assistive technology development for a more general community of people with disabilities. CCS CONCEPTS• Human-centered computing → Accessibility; Accessibility design and evaluation methods; Accessibility; Accessibility technologies.