Insufficiency fractures are a common complication of bisphosphonate use and have recently been reported in association with Roux-en-Y Gastric Bypass Surgery (RYGB). This study reports a case of a 62-year-old female, 6 years status post Mini Gastric Bypass - One Anastomosis Gastric Bypass (MGB-OAGB), presenting to our institution with bilateral groin pain of 8 months duration unresponsive to conservative management. Diagnostic workup revealed bilateral medial sub-trochanteric insufficiency fractures. She underwent bilateral intramedullary fixation with satisfactory results. This case might suggest a particular fracture pattern in patients undergoing MGB-OAGB, and raises awareness to screen patients with such presentation to rule out a fracture or to prevent the extension of an existing one.