Paul's boasting is often considered to be problematic. This paper explores Pauline boasting from the perspective of Plutarch's views on self-praise. Outlining what kinds of self-praise were and were not acceptable to someone like Plutarch, the paper analyses and positions Paul's boasting in Phil 3 in this context, concluding that, however offensive it may be to modern ears, this boasting was probably less so to the ears of his contemporaries.