Obesity, and the comorbidities associated with it, have become endemic within society. Roux-en-Y gastric bypass (RYGB) surgery is an increasingly common procedure with medical and cosmetic benefits (Li et al., 2014) [1]. However, as the case volume increases so do the rate of uncommon complications and it is imperative for surgeons to be aware of management guidelines of these complications. We present a case of Retrograde intussusception (RI) which is a rare complication status post RYGB. It is most commonly reported at the jejunojejunostomy (JJ) site, and it is hypothesized to be secondary to an antiperistaltic (retrograde) telescoping of the common limb going into the jejunal anastomosis (Varban et al., 2013) [2,3]. We present another case study as well as some points to consider in clinical management.