We report a study that investigates the role of situation awareness acquisition behaviors and decisional heuristics on mission success in a complex strategic decision making simulation. Thirty-two subjects completed a turn-based counter-insurgency scenario against a simulated adversary. Subjects played the role of a commander whose goal was to stabilize a failing state by allocating resources in various spheres of intervention like “Infrastructure development” and “Security operations”. We measured goal attainment, subjects' behaviors in terms of situation awareness, and decisional heuristics. Results show that overall performance was far from optimal. Two behaviors were positively associated with performance: system exploration behaviors at the first turn of the simulation and outcome assessment behaviors for subsequent turns. Other results suggest that the nature of the information that is sought, and the nature of the decision heuristics used, played a critical role in goal attainment. Results are discussed in terms of training and cognitive support requirements.