A series of four studies explore how the presentation of multiple items on each trial of a categorization task affects the course of category learning. In a three-category supervised classification task involving multi-dimensionally varying artificial organism-like stimuli, learners are shown a target plus two context items on every trial, with the context items' category membership explicitly identified. These triads vary in whether one, two, or all three categories are represented. This presentation context can support within-category comparison and/or between-category contrast. The most successful learning occurs when all categories are represented in each trial. This pattern occurs across two different underlying category structures and across variations in learners' prior knowledge of the relationship between the target and context items. These results appear to contrast with some other recent findings and make clear the potential importance of context-based inter-item evaluation in human category learning, which has implications for psychological theory and for real-world learning environments.