In order to help address problems of information overload currently being experienced in digital imagery domains as well as shortcomings associated with current image retrieval techniques in this research we have developed an interactive task-based approach to the capture and reuse of digital image information. Our methodology models different aspects of the relationship between images and the domain tasks that they support. This is performed by capturing and leveraging task-based context at all stages of the task execution. In practical terms this means capturing the context of a task-based query to retrieve relevant imagery as well as monitoring the interactive analysis and annotation of task-relevant imagery to gauge a measure of the usage context of the selected imagery for the particular task. Once this knowledge has been captured it becomes possible to combine and leverage these different types of context using case-based reasoning and knowledge management techniques so that they may be reused to support other users in carrying out similar image tasks.