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Tailgut cysts are rare congenital abnormalities in the retrocaecal/presacral region. Clinical diagnosis is difficult and delayed and they can present in childhood and adult life with a variety of clinical symptoms and complications. Differential diagnoses include, rectal duplication cysts, cystic teratoma, epidermal cyst, anal gland cyst and anal gland carcinoma. Magnetic resonance imaging has recently become the modality of choice to image these cysts. Although Tailgut cysts rarely undergo malignant transformation, early surgical resection is presently considered the treatment of choice. Here we report the case of a 34 year old gentleman with a Tailgut cyst associated with a Pilonidal sinus, and review of the literature. We believe that the high incidence of complications associated with operations in the presacral region should be weighed against the generally benign course of these lesions, especially with the quality of modern imaging technology.