In order to address problems of information overload in digital imagery task domains we have developed an interactive approach to the capture and reuse of image context information. Our framework models different aspects of the relationship between images and domain tasks they support by monitoring the interactive manipulation and annotation of task-relevant imagery. The approach allows us to gauge a measure of a user's intentions as they complete goal-directed image tasks. As users analyze retrieved imagery their interactions are captured and an expert task context is dynamically constructed. This human expertise, proficiency, and knowledge can then be leveraged to support other users in carrying out similar domain tasks. We have applied our techniques to two multimedia retrieval applications for two different image domains, namely the geo-spatial and medical imagery domains.