Recent research has questioned the automaticity of stereotypical thinking by identifying factors that moderate the elicitation of this process. Extending this general line of inquiry, the present experiments investigated the effects of contextual factors on stereotype activation. It was anticipated that the manner in which triggering categorical cues are encountered would moderate the activation of stereotypical thinking. Specifically, it was predicted that briefly presented primes (i.e., difficult-to-process items) would not activate sex stereotypes when they were intermixed with primes that were easy to process (i.e., items presented for longer times). The results of two experiments supported this prediction. In addition, Experiment 2 showed that stereotype activation following the presentation of easy-to-process primes is moderated by individual differences in the endorsement of stereotypical beliefs. These findings are noteworthy because they demonstrate that contextual factors modulate stereotype activation at even the very early stages of social information processing.