Background: Previous “high-stakes” examinations by the American Board of Thoracic Surgery (ABTS) required remote testing, were noneducational, and were not tailored to individual practices. Given the ABTS mission of public safety and diplomate education, the ABTS Maintenance of Certification (MOC) examination was revised in 2015 to improve the educational experience and validate knowledge acquired. Methods: The ABTS-MOC Committee developed a web-based, secure examination tailored to the specialty-specific practice profile (cardiac, general thoracic, cardiothoracic, congenital) of the individual surgeon. After an initial answer to each question, an educational critique was reviewed before returning to the initial question and logging a second (final) response. Intraexam learning was assessed by comparing scores before and after reading the critique. Diplomate feedback was obtained. Results: A total of 988 diplomates completed the 10-year MOC examination between 2015 and 2017. Substantive learning was demonstrated with an 18%, 17%, 20%, and 9% improvement in cardiac, general thoracic, cardiothoracic, and congenital final scores, respectively. This improvement was most notable among diplomates with the lowest initial scores. Fewer diplomates failed the new exam (<1% vs 2.3%). Diplomate postexam survey highlighted marked improvements in clinical relevance (35% vs 78%), convenience (37% vs 78%), and learning (15% vs 45%). Over 80% acknowledged educational value, and 97% preferred the new format. Conclusions: The new MOC process demonstrates increased knowledge acquisition through a convenient, secure, web-based practice-focused examination. This approach provides feedback, identifies baseline knowledge gaps for individual diplomates, and validates new knowledge attained.