Pilonidal disease is a chronic skin and subcutaneous infection emanating from the center of the natal cleft, often extending to the buttocks. It is more common in males than females and usually occurs between the time of puberty and 40 years of age. A common theory is that pilonidal disease is caused by an ingrown hair at the center of the cleft resulting in inflammation and infection extending to the buttocks. Presentation of the pilonidal disease can range from an asymptomatic cyst or midline pits to chronically inflamed cyst, large open wounds in the midline, long draining sinus tract, or an acute abscess. Only in exceptionally rare cases is imaging required. Treatment depends on the disease pattern. An acute abscess is treated with drainage and antibiotics, while a complex or recurring infection is treated surgically with either excision of a cyst or unroofing of a sinus tract. Reconstructive flap techniques such as the Bascom cleft lift procedure, Karydakis flap, rhomboid, or Z-plasty can be done to reduce the risk of recurrence by leaving less scar tissue and flattening the region between the buttocks. Recent data has suggested that off-midline incision closure may lead to a lower risk of recurrence. Here, we present the case of a male patient who had previously had flap surgery for the pilonidal disease, but experienced recurrence and the development of a sinus tract. Due to the extensive nature of the disease, a deep flap was required to mobilize tissues and close the eventual wound. A deep flap like this is often only required in re-do surgery, rather than for primary disease, for which only a 1-cm subcutaneous flap is required.