Stroup was born in Anderson, South Carolina, the daughter of Judith and Don Stroup, a senior vice president at MUFG Union Bank. She spent her childhood in Charlotte, North Carolina. She graduated from Providence High School in 2004. Stroup received a full scholarship to attend the University of Georgia, but declined in order to pursue an acting career.
Stroup's first acting role was a guest appearance on a 2005 episode of Unfabulous. Stroup has since appeared in a number of other TV shows, such as Grey's Anatomy, October Road, and True Blood. In 2007, Stroup appeared in 4 episodes of Reaper, in which she played the protagonist's ex-girlfriend. She appeared in a number of small independent movie productions, such as Left in Darkness, Pray for Morning, Vampire Bats.
In March 2007, Stroup starred as the female lead in The Hills Have Eyes 2. Stroup played the role of a US Army National Guard soldier named Amber who fights for survival with her peers against a group of mutant people. The film was a fast-forward sequel to The Hills Have Eyes, a remake of the 1977 movie of the same name. Despite negative reviews from critics the film went on to gross over $67 million worldwide. That same year Jessica had a supporting role in This Christmas.

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