Purpose: Health professions education (HPE) emphasizes growth, resilience, and second chances, yet little attention has been given to whether different educational environments create different psychological demands for learners. Across 2 studies examining challenge engagement in physician assistant (PA) and HPE doctoral learners, we found the relationships among mindset, goal orientation, and fear of failure differed across educational contexts despite using a common theoretical framework and measurement approach. Methods: Findings from 2 complementary studies on the Challenge Engagement Inventory, a psychological disposition to engage with or avoid difficult learning experiences, will be shared. In study 1, we developed and evaluated the CEI, a measure integrating mindset, goal orientation, and fear of failure among PA students (n=220) using exploratory structural equation modeling. Study 2 applied the same theoretical framework & inventory to HPE students (n=35) using exploratory PCA after unsupported confirmatory approaches. Results: Mindset, goal orientation, and failure fear emerged as contributors to challenge engagement; yet, the relationships differed across settings. In both groups, fear of failure and performance-oriented goals remained closely related, but mastery orientation and the overall motivational structure differed between them. PA education is characterized by structured curricula and frequent high-stakes assessments, HPE PhD centers on prolonged independent scholarship with fewer discrete failure events but greater ambiguity. Overall, challenge engagement may be influenced by learner dispositions and the nature of the educational challenges learners navigate. Conclusion: Supporting learner growth requires intentionally preparing them for the psychological demands of the educational environments we create. Assessment-driven and project-driven programs may require different approaches to feedback, mentoring, remediation, and learner support.