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Introduction: Acute gallstone pancreatitis is a potentially severe disease associated with morbidity and mortality. Cholecystectomy is recommended to prevent recurrence. During pregnancy, surgical management is challenging, and in the post-partum period small gallstones may spontaneously disappear. Ursodeoxycholic acid (UDCA) is safe during the last 6 months of pregnancy and effective in dissolving small gallstones, although recurrence after discontinuation is common in the general population. The optimal strategy to prevent recurrent acute pancreatitis during and after pregnancy remains unclear. Methods: Between 2002 and 2017 we prospectively treated women with acute pancreatitis related to small gallstones (≤1 cm in diameter) during the last six months of pregnancy or within the first post-partum year who declined surgery. Patients received UDCA until stone dissolution. A patent cystic duct was confirmed by ultrasonography; after delivery, a non-contrast CT scan was performed to exclude calcified stones. Patients were followed for at least 6 years or until recurrence, with serial clinical and ultrasonographic examinations. Results: UDCA was associated with complete dissolution in 13/14 women within a mean ± SD of 7.77 + 3.1 months. One patient experienced gallstone recurrence 75 months after treatment discontinuation. Two patients developed recurrent pancreatitis (at 1 and 88 months respectively). Twelve women remained free of recurrence over a mean ± SD follow-up of 79.5 + 9.4 months. Discussion: This is an observational study in which we document that UDCA may facilitate the spontaneous dissolution of small gallstones after delivery and can be considered a bridge strategy during pregnancy when surgery is not feasible. However, this study cannot determine the additional benefit of UDCA over the spontaneous disappearance of stones observed after delivery because we had no control group. Cholecystectomy remains the standard of care post-partum. Medical therapy should be reserved for women who refuse surgery and it requires close ultrasonographic surveillance. The main strength of this study is the prospective long-term follow-up of a consecutive cohort with a rare condition. Limitations include the small sample size, missing control group and single-center design.