The effect of choice bracketing — the consideration of repeated decisions as a set versus in isolation — has important implications for products that are inherently time-sensitive and entail varying levels of risk, including retirement accounts, insurance purchases, and lottery preferences. We show that broader choice brackets lead to more optimal risk preferences across all risk types, including negative expected value and pure-loss gambles, suggesting that broad decision framing can help individuals make better choices over risks more generally. We also examine the mechanism behind these bracketing effects. We find that bracketing effects work by attenuating (magnifying) the weight placed on potential losses for positive EV (non-positive EV) gambles and by providing aggregated outcomes that might not otherwise be calculated. Thus, decision frames that provide probability distributions or aggregated outcomes can help individuals maximize expected value across different types of risky prospects.