The present study outlines the development and initial validation of a conditional reasoning test for risk and incident propensity (CRT-RIP). Individuals carry with them a wide array of experiences, attitudes, and dispositions that may influence their proneness for risk-taking and incident involvement. Yet, measuring risk propensity has proven challenging due to the high levels of transparency found in the self-report measures that are presently available. We initially developed 28 conditional reasoning items to measure risk and incident propensity. With four developmental samples, we evaluated item characteristics. After applying item decision guidelines for conditional reasoning tests, we retained 14 items. Using three test samples and with the 14-item CRT-RIP, we assessed predictive and incremental validity over five-factor personality traits and an explicit, self-report measure of risk propensity. With one final sample, we provided further validation of the 14-item CRT-RIP. Findings demonstrate initial success in predicting various safety behaviors and outcomes. Ability to measure risk propensity and to predict safety behaviors is valuable because of the profound consequences that may proceed failure to enact safety behaviors including property damage, injury, illness, or even death. We discuss potential applications and suggest directions for future research. (PsycInfo Database Record (c) 2024 APA, all rights reserved).