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Herpes Simplex Virus (HSV) is an uncommon cause of esophagitis and particularly so in immunocompetent individuals. While the common presentation tends to be odynophagia and/or dysphagia, fever, and retrosternal chest pain, there are variations and rarely it can present more ominously as esophageal rupture. We report a rare case of esophageal perforation with penetration into vertebral space secondary to chronic HSV esophagitis in a 71-year-old immunocompetent female. This is the second known such occurrence. The patient had a long stay in hospital but recovered from the condition and was followed up for one year after initial presentation.