The present study examined how training difficulty interacts with individual differences in visual processing strategy. Participants discriminated between random polygon stimuli that varied both in both complexity and similarity. Individual processing strategies were categorized into either “holistic” or “analytic” strategy types based on the discrimination latency as a function of polygon complexity. Training difficulty was defined by the similarity of the stimuli being discriminated. Both strategy groups discriminated between similar (“hard” training) or dissimilar stimuli (“easy” training) and then between novel polygons in a transfer stage. Results showed that individual differences in processing strategy interact with training difficulty to influence performance on transfer to novel stimuli. The effect of training on transfer performance was greater for the participants with a holistic strategy than for those with an analytic strategy. The implications for training and display design are discussed.