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Gradenigo’s syndrome is defined by the classic clinical triad of ear discharge, trigeminal pain, and abducens nerve palsy. It has become a very rare nosological entity after the introduction of antibiotics, so that has been defined as the “forgotten syndrome.” However, the underlying pathological process (apical petrositis) still represents a life-threatening condition that shall be immediately recognized in order to address the patient to the proper therapy. The therapy itself may be an argument of discussion: on a historical background ruled by surgery, reports of successful conservative antibiotic treatment have risen in recent years. We reported a case of Gradenigo’s syndrome in a child with an abscess of the left petrous apex and initial involvement of the carotid artery. After multidisciplinary evaluation, we decided to encourage conservative treatment, until complete regression was observed. The available literature of the last 10 years was reviewed, with particular attention to the presence of an apical abscess and the therapeutic approach. The principles of management with regard to conservative therapy versus surgical indications are therefore examined and discussed.