Digital imagery pervades modern life. More than a billion images per day are produced and uploaded to social media sites, and we also encounter digital images within websites, apps, digital documents, and eBooks. Engaging with digital imagery is part of the fabric of participation in contemporary society, including education, the professions, e-commerce, civic participation , entertainment, and social interactions. However, most digital images remain inaccessible to the 39 million people worldwide who are blind. This project explores how innovations at the intersection of AI and HCI can increase image accessibility for people who are blind, including addressing questions such as what details should be included in automated image descriptions, how these details should be presented to the end-user, and how to operationalize and convey the possibility of error in automated captions.