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Rathke cleft cysts (RCCs) are benign epithelial sellar and suprasellar lesions arising from remnants of Rathke pouch. Although typically incidental and asymptomatic, intracystic hemorrhage is rare and may mimic pituitary adenoma apoplexy. We report a 19-year-old woman presenting with one week of progressive severe headache. CT demonstrated sellar enlargement with suprasellar extension. MRI showed a hemorrhagic sellar lesion centered in the pars intermedia/posterior pituitary with fluid-fluid levels, dependent T2 hypointense components, susceptibility-related signal loss, and suprasellar extension abutting the optic chiasm, without nodular enhancement. Neurologic, ophthalmologic, and endocrinologic evaluations were unremarkable. Conservative management with corticosteroids and observation was pursued. Follow-up MRI at 3 months demonstrated markedly decreased pituitary enlargement with evolution into a small residual nonenhancing pars intermedia cyst, suggesting a hemorrhagic RCC. Recognition of this rare entity may support conservative management and avoid surgery in clinically stable patients.