“U Should’ve Known Better” is a song by American recording artist Monica. It was written in collaboration with Harold Lilly and Jermaine Dupri, and produced by the latter along with frequent co-producer Bryan Michael Cox for her original third studio album, All Eyez on Me (2002). When the album was shelved for release outside Japan, the song was one out of five original records that were transferred into its new version, After the Storm (2003). A contemporary R&B slow jam, “U Should’ve Known Better” contains elements of soul music and rock music. Built on an pulsating backbeat, the song’s instrumentation consists of screeching guitars and an understated harp pattern. Lyrically, Monica, as the protagonist, delivers a message of loyalty to her imprisoned love interest and sings about staying down for him despite his doubts.