While posterior vaginal compartment prolapse and defecatory dysfunction are highly prevalent conditions in women with pelvic floor disorders, the relationship between anatomy and symptoms, specifically obstructed defecation, is incompletely understood. This review discusses the anatomy of the posterior vaginal compartment and definitions of defecatory dysfunction and obstructed defecation. A clinically useful classification system for defecatory dysfunction is highlighted. Available tools for the measurement of symptoms, physical findings, and imaging in women with posterior compartment prolapse are discussed. Based on a critical review of the literature, we investigate and summarize whether posterior compartment anatomy correlates with function. Definitions of obstructed defecation and significant posterior compartment prolapse are proposed for future exploration.