Dawn Penn (born Dawn Pickering, 1952, Kingston, Jamaica) is a Jamaican reggae singer.

Dawn Penn's earliest recordings were for Prince Buster around 1966. In 1967 she recorded and released the rocksteady single, "You Don't Love Me" produced by Coxsone Dodd at Studio One. She also recorded "Why Did You Leave" at Studio One, "Broke My Heart" for Bunny Lee, "I Let You Go Boy" and covers of "To Sir with Love" and "Here Comes the Sun".

By 1970 Penn had left the music industry and had moved to the Virgin Islands. In 1987, however, she returned to Jamaica and to music.

In the summer of 1992 she was invited to appear on stage at a Studio One anniversary show, where she performed the song "You Don't Love Me" with Steely