This chapter provides a literature review of the role of imaging in the diagnosis and management of pineal tumors and cysts and other masses of the pineal region. Several types of lesions are illustrated. Imaging plays a pivotal role in the diagnostic workup, surgical planning, and follow-up. Computerized tomography plays a role in the emergency setting, owing to its wide availability. It is able to detect obstructive hydrocephalus, mass calcification, and hemorrhage. Magnetic resonance imaging is the modality of choice for tumor characterization and pretherapeutic planning. Pineal cysts are common, and most cases do not require imaging follow-up. However, atypical findings may give diagnostic problems with partially cystic tumors. High-resolution sequences, multiplanar views, and contrast injection are needed. Advanced sequences including diffusion-weighted imaging, apparent diffusion coefficient, susceptibility-weighted imaging, spectroscopy, and flow sensitive sequences may provide useful information. Spine MRI is mandatory whenever a malignant pineal tumor is suspected. Preoperative imaging should also include careful analysis of vascular anatomy, and CTA or MRA has reduced the need for invasive angiography. Unfortunately, in many cases imaging findings are still not specific of a tumor type, and then definitive diagnosis relies on serum or cerebrospinal fluid tumor markers and histological and immunohistochemical analyses.