This case involves a 16-year-old female, Kayla, who presented to the emergency department twice with severe pelvic pain. The first attending physician diagnosed her with pelvic inflammatory disease (PID) based on her symptoms and sexual history. However, her pain continued to worsen despite antibiotics. When consulted, the gynecology team discovered she actually had ovarian torsion requiring surgical removal of her ovary. This case highlights how diagnostic errors can occur from cognitive biases, lack of thorough history and exam, and failure to consider alternatives to the initial diagnosis. It is important for physicians to reflect on errors to improve care and prevent future mistakes.