Contemporary scholars, extending back to Hans Windischʼs 1924 commentary on 2 Corinthians, have pointed to parallels between Paulʼs language of ‘boasting’ in 2 Cor 11–12 and Plutarchʼs treatise de laude ipsius. But would an ancient reader have made this connection between Paulʼs letters and discussions about self-praise (πϵριαυτολογια) in ancient rhetorical and philosophical writings? This paper demonstrates that John Chrysostom, the rhetorically trained Antiochene, did just that, particular in his fifth oration de laudibus sancti Pauli, where he defends Paulʼs ‘speech about himself’ on precisely the grounds Plutarch allowed for inoffensive boasting in his famous treatise.