Access to digital images is important to people who are blind or have low vision (BLV). Many contemporary image description efforts do not take into account this population’s nuanced image description preferences. In this paper, we present a qualitative study that provides insight into 28 BLV people’s experiences with descriptions of digital images from news websites, social networking sites/platforms, eCommerce websites, employment websites, online dating websites/platforms, productivity applications, and e-publications. Our findings reveal how image description preferences vary based on the source where digital images are encountered and the surrounding context. We provide recommendations for the development of next-generation image description technologies inspired by our empirical analysis.