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Security decision-making is hard for both humans and machines. This is because security decisions are context-dependent, require highly dynamic, specialized knowledge,and require complex risk analysis. Multiple user studies show that humans have difficulty making these decisions, due to insufficient information and bounded rationality. However, current automated solutions are often too rigid to adequately address the problem and leave their users more confused and inept when they fail. A mixed-initiative approach, in which users and machines collaborate to make security decisions and make use of complementary strengths rather than weaknesses, is needed.