In a digital image annotation and retrieval system, a machine learning model identifies an image feature in an image and generates a plurality of question prompts for the feature. For a particular feature, a feature annotation is generated, which can include capturing a narrative, determining a plurality of narrative units, and mapping a particular narrative unit to the identified image feature. An enriched image is generated using the generated feature annotation. The enriched image includes searchable metadata comprising the feature annotation and the plurality of question prompts.