What are the practices and approaches to cataloguing and keywording used to manage the wide variety of imagery found in a specialist picture library? How can keywording protocols be effectively implemented and what tools can be created to aid this process? This presentation will examine these questions by studying specific images, discussing examples of good (and bad!) keywording practice, specifically in the environment of a specialist library collection. The importance of a keywording structure (where less is often more) and the practicalities of providing metadata for image supply to international partners will also be discussed. The presentation will close by looking at the feasibility of more automation in the keywording process within a specialist collection and the major lessons Mary Evans Picture Library has learned in moving from an analogue archive to a fully digital online presence.