Treatment of biliary-enteric (B-E) anastomotic stricture is difficult, often requiring protracted management via several procedures. Stricture restenosis is a common issue; paclitaxel drug coated balloons (DCB) have been shown to reduce restenosis via an antiproliferative mechanism in peripheral arterial disease applications; use of these devices may reduce lesion restenosis in anastomotic strictures. In this study, we seek to evaluate the efficacy of DCB treatment of B-E anastomotic strictures. Patients who underwent treatment of B-E anastomotic strictures with DCB from 9/2016 to present were reviewed. Patients received initial percutaneous drain placement; approximately 1 week later standard/cutting balloon angioplasty and 7 mm DCB application for 3 minutes at nominal inflation was performed. Symptom improvement was qualitatively assessed. Alkaline phosphatase (AP) and total bilirubin (TBili) values were collected prior to initial biliary intervention and following DCB cholangioplasty. Paired t-test was performed; significance was determined at p <0.05. Six patients (5M:1F, mean age 70) with B-E anastomotic strictures treated with DCB were identified; technical success was achieved in 5; these patients experienced symptomatic improvement. One patient had B-E stricture at a transplant hepaticojejunostomy. Four patients were found to have benign strictures, one patient had a malignant stricture and represents the only treatment failure. Prior to internal/external drain placement and DCB cholangioplasty, the average TBili was 3.8 ± 1.9 (mean ± SEM), which trended downward to 1.4 ± 0.6 (mean ± SEM) following DCB therapy (p = 0.08). Prior to internal/external drain placement and DCB cholangioplasty, the average AP was 439 ± 136 which decreased to 262 ± 77 (p = 0.03). No complications were encountered in this series. DCB cholangioplasty demonstrates early promise in the treatment of benign biliary-enteric anastomotic stricture. Further study needs to be performed to validate these findings and precisely define patients that could benefit from this intervention.