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Pigtail catheters and chest tubes are commonly used for effective resolution of pneumothoraces and drainage of simple pleural effusions. Given their small calibers, better flexibility and more ease at the time of insertion, pigtail catheters are associated with lower risks of complications when compared to traditional chest tubes. Commonly reported complications of the pigtail catheters include the higher probability for clogging, kinking, and obstruction. Rare complications as air embolism, penetration of the heart and transection of the lungs are seldom reported in the literature. We present a case of an 81-year-old female presented with covid-19 pneumonia who developed bilateral spontaneous pneumothoraces requiring bilateral pigtail insertion. The patient developed worsening hypoxia and chest imaging revealed that the left pigtail was transected into the lung parenchyma. With this case report, we hope to bring to light a rare complication of pigtail placement.