Uncertainty abounds in the clinical environment. Medical students, however, are not explicitly prepared for situations of uncertainty in clinical practice, which can cause anxiety and impact well-being. To address this gap, we sought to capture how students felt in various clinical scenarios and identify programs they found helpful as they worked through uncertainty in their clerkships to better inform curriculum that prepares them to acknowledge and navigate this uncertainty. This is an observational cross-sectional study of third-year medical students surveyed at the end of core clerkships. The survey consisted of the General Self-Efficacy (GSE) Scale and Intolerance of Uncertainty Scale (IUS). Items asked students to rate preparedness, confidence, and comfort with uncertainty in clinical practice. Items on curricular programs asked students to identify training that prepared them for uncertainty in clerkships, and examined correlations with specific clinical practice uncertainty domains (CPUDs). Spearman’s rank-order correlation, Chi-Square, and ANOVA were used to analyze quantitative data. Open responses were analyzed using Braun and Clarke’s Framework. Response rate was 98.9% (287/290). GSE was inversely correlated with IUS (p < 0.001). GSE was positively correlated with all CPUDs (p < 0.005). IUS had an inverse correlation with all CPUDs (p < 0.005). Pedagogies with statistically-significant relationships with preparing students for uncertainty, communicating and building relationships with patients during times of uncertainty, and overall well-being included: team debriefs, role plays, case- and team-based learning, story slams, and sharing narratives with peers and faculty (p < 0.05). Qualitatively, students appreciated storytelling, role-modeling of communication strategies, debriefing, and simulations. Strategically immersing specific educational formats into formal curriculum may help cultivate skills needed to prepare students for uncertainty. Clinical debriefs, interprofessional role plays, simulations, communications skills training, instructor emotional vulnerability, storytelling, and peer-to-peer conversations may have the most impact. Further study is required to evaluate their longitudinal impact.