Research regarding the description-experience gap is extended by the re-examination of four components. The first further observed the role of description when accompanying experiential presentation, while the second sought to add an additional dimension to opposing patterns seen between decisions from description (overweighting of small probabilities) and sequential experience (underweighting rare events). The added experiential condition of simultaneous experience controls for sample size and recency effects, and presents a matrix of outcomes precisely representing outcome probabilities. The third considered complex decision making, with options having 4 or 5 outcomes to consider and compare, such as seen in more real-world decisions, and the final aim was to examine the difference between these decision choices in altered context-frames. Study 1 was designed to equate to previous experimental investigations involving choices between lotteries, while study 2 was intended to inspect these differences in a real-life risk setting, and was situated in a medical context frame. It was found that in both studies there were differences between description and simultaneous experience, which followed a similar pattern of description decision makers presenting more risky behaviour. These differences were predominantly seen when the options were more complex and outcomes could not be directly compared, and it is suggested that in these cases, participants were more open to using the experiential information to aid decision making and consequently more susceptible to exhibit behaviour which underweighted small probabilities. It was also seen that participants implemented less risky behaviour when choices were observed in a medical context frame.