We sought to examine the potential differences between different types of risky decisions. While some decisions are easily represented as choices between future alternatives, other decisions may be better represented as the management of a personally owned situation. Schneider (2003) created the risk management task, which manifested these situated improvement decisions, and identified a unique pattern of risk preferences when compared to the standard gambling paradigm. To determine what cognitive processes might be differentially activated for each type of decisions so as to yield these risk preference differences, we incrementally manipulated the gambling paradigm to parse potentially influential elements of situational context from both risky choice and risk management. The elements of context found to be influential were (a) making an improvement of your situation rather than a choice within your situation, (b) integrating information into a more compact display, and (c) limiting the visual salience of consequence information. The implications of these results as they relate to current formal models of decision making and subsequent investigations of decision context are addressed. Future directions using a similar appreciation of individual perceptual and cognitive processes when studying decision making are also discussed.