Attending the Advanced Naval Communications School (ANCS), Lt. Barbara O’Leary intends to develop her professional skills and cast aside her ’Plain Jane’ persona. However, Kirsten, who earns her living as an ’intimate companion’; Simon, a corrupt businessman; and Captain Lemaire, the ANCS chief with wandering eyes disrupt Barbara’s plans. Soon she finds herself caught up in a bizarre under-cover investigation directed by Roger Bockman, an overly ambitious DOJ attorney. A holiday trip to discover Simon’s bosses gives Ahmed, Barbara’s half-brother and terrorist mastermind, his opportunity to strike, first, in the Guatemalan jungle, and, later, in East Texas. In The O’Leary Entanglement terrorism, corruption, lust, and marital infidelity inexorably transform Barbara’s personal growth opportunity into an adventure that threatens her career, her reputation, and her very existence.