Aviation accidents are rare and often triggered by surprising atypical events, often where important data do not get noticed or attended. Yet most psychological research on attention and human response deals with and statistically analyzes "typical" or "average" behavior, not the psychology of surprise. We emphasize the relevance of attention to safety, to automation, and to the psychology of surprise and briefly summarize some research on automation and free flight that highlights this linkage. Implications for design, training and modeling and research are then described.