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).

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.

In an interview with MTV News in June 2000, Monica revealed that she was planning to start work on a follow-up to her 1998 album The Boy Is Mine throughout the summer season, with a first single to be released by October of the same year.

[1] The following month, personal tribulations put a temporary halt on the album's production when her former boyfriend Jarvis "Knot" Weems committed suicide.

[3] Throughout the process, Monica primarily worked with her usual stable of producers, which included Dallas Austin, production team Soulshock & Karlin, Bryan Michael Cox, and Rodney Jerkins and his Darkchild crew.

[5] William Odum played the guitar, while recording at the SouthSide Studios in Atlanta, Georgia was overseen Brian Frye.

[6] Although a duet with DMX, "Don't Gotta Go Home", was expected be released as the album's fourth single at times, "U Should've Known Better" eventually replaced original plans.

The video follows the single's topic of a misunderstandings in a relationship, showing Monica as the girlfriend, with the boyfriend held in a Mexico hold-prison.