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Risk propensity (RP) is a trait characterized by an increased probability of engaging in behaviors that have some potential danger or harm but also provide an opportunity for some benefit. In the present study, a new RP task with several dilemmas was explored. Each dilemma includes the initial set plus successive approximations for estimating the Indifference Value between a Secure and the expected value of an uncertain Game. The scores showed good internal consistency, reasonably test-retest reliability, and good validity. The risk propensity dilemmas (RPD) task is proposed as an addition to an ideal battery of tasks for reflecting a complex trait that should be assessed from varied perspectives, procedures, and scenarios of uncertainty.