Background Duodenal stump fistula (DSF) is a severe complication of gastrectomy. Although nonsurgical therapy is preferred, surgery is still mandatory in one third of DSF patients. The aim of this article is to analyze the surgical management of DSF and factors related to its outcome. Methods We performed a retrospective multicenter study using data from January 1990 to November 2011 in 16 Italian surgery centers. We collected 8,268 elective gastrectomies for malignancies, 7,987 by the laparotomic and 281 by the laparoscopic approach. Two hundred five patients developed a DSF, 75 of whom underwent surgery for DSF. We analyzed mortality and DSF healing time as well as the impact of clinical, oncological, and surgical characteristics. Results The laparoscopic approach increased the risk of DSF development (odds ratio 5.6, 95 % confidence interval 2.7–10.6, P  < 0.001). The indication for first DSF surgery was intra-abdominal sepsis; the failure rate was over 30 %, associated with the appearance of fistulas of neighboring organs, bleeding, and the need for reoperations. The mortality rate was 28 % and was related to the presence of vascular disease ( P  = 0.04), more than one reoperation ( P  = 0.05), sepsis ( P  < 0.001), and renal failure ( P  < 0.001). Fifty-four patients recovered after a median of 39 days (interquartile range 22–68 days); the need to perform more reoperations ( P  < 0.01) and the presence of an abdominal abscess ( P  < 0.01) led to an increase in healing time. Conclusions Surgery for DSF has a poor prognosis. Our data will help to identify patients at risk of death, but unfortunately could not establish the best surgical procedure applicable to all cases of DSF.