Human decisionmaking does not typically fit the classical analytic model, and the heuristics employed may yield a variety of biased judgments. These biases are often considered inherently adverse, but may be functional in some cases. Decision support systems can mitigate some biases, but often introduce others. “Debiasing” decision support systems entails designing DSS to address expected biases, and to preclude inducing new ones. High-level C2 decisionmaking processes are poorly understood, but these general principles and lessons learned in other fields are expected to obtain. A notional air campaign illustrates potential biases in a commander’s judgment during planning and execution, and the role of debiasing operational DSS.