"Shoulda Let You Go" is a song by American R&B singer Keyshia Cole.

The song features additional vocals by rapper Amina.

"Shoulda Let You Go" premiered on August 25, 2007, on V103, an Atlanta-based radio station, and was later released as the album's second single.

The video was shot in Miami and directed by Erik White.

The video begins with Cole sleeping as we see roses and an answering machine showing that she has been given ten missed calls and twelve unread messages from her ex.