The Penitent Saint Jerome with a Young Monk is a painting by the Italian Renaissance painter Filippo Lippi, dating to c. 1439.

The work could be identified with the Saint Jerome Penitent of which Lippi asked payment in a letter issued to Piero de' Medici in 1439.

It is a small panel, divided into two different scenes: in the upper part is Saint Jerome with the wooden cross, the stone to strike his breast and the lectern lying on the rock.

In the lower part, with a chronological step, is the episode of the saint with the lion having a thorn in the paw.

The unfriendly landscape is a metaphor of the hermit style of life.