Heuristics--cognitive shortcuts used in decision-making events--have been paradoxically praised for their contribution to decision-making efficiency and prosecuted for their contribution to decision-making error (Gigerenzer & Gaissmaier, 2011; Gigerenzer, Todd, & ABC Research Group, 1999; Kahneman, 2011; Kahneman, Slovic, & Tversky, 1982). Recent research in outdoor adventure education (OAE) using the heuristic concept to diagnose fieldbased decision-making errors has ignored this duality, focusing solely on the negative potential of heuristic processing (e.g., Clement, 1997; McCammon, 2004a; Simenhois & Savage, 2009; Tremper, 2008; Wheeler, 2008) and neglecting positive and prudent uses of heuristic processing in field-based risk management. This conceptual manuscript follows the suggestion of Furman, Shooter, and Schumann (2010) to explore the dual-nature of heuristic processing in OAE. Using a dialectical method, the authors interrogate the dominant, negativistic interpretation of heuristic processing as well as illustrate the common uses of heuristics in risk management curricula within outdoor pursuits. In the resulting synthesis, the authors show that a "symptom-prescription" view of heuristic duality can reclaim the utility of heuristics as decision-making aids (e.g., scenarios, mnemonics, visual models) in OAE, as well as provide implications for decision-making scholarship and field-based practice.