Drawing from in-depth interviews with 52 active street criminals, this article examines the grounded theoretic implications of bounded rationality for retaliatory street violence. The bounds on rationality that this article explores are anger, uncertainty, and time pressure. These bounds create imperfections in the retaliatory decision-making process that, in turn, cause asymmetries in the way that reprisal is enacted. Two asymmetries are operative in this regard: strike intensity and target choice. Anger produces asymmetries of both types. Uncertainty and time pressure produce only target-choice asymmetry. All three modalities cause retaliation to be redirected. Redirection promotes the spread of urban violence through conflict spirals.