Research indicates that many of the benefits of visual aids follow from scaffolding of cognitive and metacognitive processes that enable independent evaluation and understanding of risk—i.e., risk literacy (see Skilled Decision Theory; Cokely et al.,. 2012; in press). Here, we begin with a brief review of theoretical foundations of the current tutor based on graph comprehension theory. Next we discuss key steps in developing and validating our pseudo-intelligent adaptive tutor with emphasis on cognitive and psychometric item analyses and transfer assessments (i.e., decision-making biases). Finally, we present recent changes in technical implementation of the RiskLiteracy.org platform (i.e., Python based with a NoSQL database) that are designed to facilitate development of dynamically interactive, yet brief (5 minute to 3 hour) and easier-to-develop training and risk communication tutors. Discussion focuses on emerging opportunities including cognitive-oriented usability analyses that should help promote an effective, enjoyable, and inclusive user experience.