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Representation of persons from diverse backgrounds remains a persistent challenge for medicine and dentistry workforces. Past research has focused on quantifying factors such as markers of educational achievement to explain the difficulty of increasing diversity within the professions. There has been less effort toward understanding the perspectives of undergraduate students on the threshold of applying to medical/dental school about distinct barriers to pursuing a medical or dental career and continuing through the training pipeline.In 2012 and 2013, the authors conducted a qualitative study of undergraduate students participating in the Tour for Diversity in Medicine, a program where minority physicians and dentists visit colleges with large fractions of minority students to encourage careers in the health professions. Focus groups were convened during the visits to examine perceived barriers to pursuing careers in medicine and dentistry and challenges identified through thematic content analysis.Eighty-two students participated in discussions at 11 colleges visited between September 2012 and February 2013. Students described challenges including inadequate institutional resources (e.g., sparse clinical opportunities), strained personal resources (e.g., conflict arising from familial pressure), inadequate guidance and mentoring to assist with key career decisions, and societal barriers. For participants, these challenges caused them to question the viability of persisting in the pipeline to a medical or dental career.Solving the issue of diversity in medicine and dentistry is multifaceted, but elucidated challenges from the undergraduate student perspective offer targeted areas where intervention may help remedy barriers and decrease pipeline leakiness.