Background Medical trainees must learn how to provide effective feedback as an essential communication skill, yet few models exist for training and assessing these skills. Objective To develop an observed structured feedback examination (OSFE) to provide feedback training to pediatric fellows and assess changes in skills and self-reported confidence. Methods This educational study was conducted from 2019 to 2020 at an academic children's hospital. Our team developed the OSFE and trained standardized feedback recipients and faculty. Fellows completed baseline self-assessments (31 items) on prior exposure to feedback training, application of skills, and confidence. They then participated in the OSFE, giving feedback to a standardized recipient using a standardized scenario, and were scored by faculty and recipients using a 15-item checklist for performance. Next, fellows participated in feedback training and received individualized feedback, after which they repeated the OSFE and confidence self-assessment. Three months later, fellows completed self-assessments on confidence and application of skills and another OSFE to assess retention. Descriptive statistics and signed rank sum test were used for analysis. Results Of 60 eligible fellows, 19 participated (32%), with 100% follow-up. After training and individualized feedback, all fellows improved feedback skills as measured by OSFE performance (mean change +0.89). All items, measured on a 5-point Likert scale, were sustained 3 months later (mean change +0.92). All fellows reported improved confidence in feedback knowledge (mean change +2.07 post, +1.67 3 months post). Conclusions Feedback training using simulation and individualized feedback moderately improved fellows' performance, confidence, and 3-month retention of feedback skills.