Masses in the Parotid tail can be source of consternation to radiologist and clinicians and therefore need attention. Inaccurate localization may lead to significant iatrogenic complications. Anatomically localization lesions of Parotid tails is of relevance as it often creates radiological confusion, as was in this case also. Imaging features of Parotid tail involvement need to be reviewed for, proper understanding and discussed with radiologist for complication free management. A Clinico-radiological correlation reviewing 111 such cases was found which described pleomorphic adenoma(15) , Warthins tumor (14) , infective pathologies, Sjogren disease and also malignant lesions in 27 cases. The notable radiological findings in the cases where enhancement, multiplicity of lesions, on CT and diffusion weighted (varied) signal intensity of MR changes. Relationship of parotid tail/ lesions with surrounding structures like facial nerve or its branches , sternocleidomastoid muscle and posterior belly of digastric muscle, proximity close to the level II LN and posterior part of submandibular salivary gland all need to clearly examined and analyzed. Such a lesion has been referred to as Earring lesions in literature. Earring lesion is best appreciated and less confusing in coronal images and equally challenging in palpation. Though rare, localizing anatomical features of parotid tail lesions are reviewed in this paper along with a case report of parotid tail tumor.