Weight regain occurs in a significant number of patients following gastric bypass1 and continues to be a potential Achilles heel of the gastric bypass procedure. In this issue of JAMA Surgery, Wood et al2 provide an extensive case series with admirable follow-up to examine clinical factors associated with weight regain. Beyond the usual suspects (baseline body mass index [calculated as weight in kilograms divided by height in meters squared] and age3), the study suggests an association between insulin use and better long-term weight loss. This is counterintuitive, as diabetes and insulin use are associated with weight gain4 and poorer surgical outcomes.5 Wood et al2 found no increase in health care visits for insulin-dependent patients postoperatively in the study to account for these findings, and there was similarly no increased use of diabetes medications with weight loss effects. Interestingly, the study also found that patients receiving more than 12 medications were more likely to be successful in long-term weight loss.2 Combined, this appears to suggest that some of the sickest patients have the best outcomes after surgical procedures, a finding that would be new to the literature.