Common diagnostic challenges in gynecology and the role of imaging in their evaluation are reviewed. Etiologies of abnormal uterine bleeding identified on pelvic sonography and sonohysterography are presented. An algorithmic approach for characterizing an incidentally detected adnexal mass and use of magnetic resonance imaging for definitive diagnosis are discussed. Finally, the role of F18-fluorodeoxyglucose positron emission tomography in the management of gynecological malignancies, and pitfalls associated with their use are examined.