<p>Vasovagal syncope is the most common medical emergency encountered in dental practice and is typically benign. However, recurrence during the same operative session may present with escalating severity and misleading clinical recovery. This article reports a clinical observational case of recurrent vasovagal syncope occurring during a complicated mandibular third molar extraction in an anxious patient with a documented prior history of syncope. Two consecutive episodes occurred during the same session, the second associated with transient loss of consciousness. A subsequent appointment, managed through early prodromal recognition and conservative autonomic stabilization, allowed safe completion of treatment without syncope. This report emphasizes sustained nociceptive input, emotional stress, hypersalivation as a parasympathetic prodromal marker, and premature resumption of treatment as critical contributors to recurrence. A pathophysiological model of vasovagal recurrence and severity escalation adapted to dental practice is proposed, with practical implications for prevention and management.</p>