Intraperitoneal prophylactic drain (IPD) use in distal pancreatectomy (DP) is still controversial. A survey was carried out through the Italian community of pancreatic surgeons using institutional emails, Twitter, and Facebook accounts of the Italian Association for the Study of the Pancreas (AISP) and the Italian Association of Hepato-biliary-pancreatic Surgery (AICEP). The survey was structured to learn surgeons’ practice in using IPD through questions and one clinical vignette. Respondents were asked to report their regrets for omission and commission regarding the IPD use for the clinical scenario, eliciting a scale between 0 (no regret) and 100 (maximum regret). The threshold model and a multilevel mixed regression were built to identify respondents’ attitudes. One hundred six surgeons completed the survey. Sixty-three (59.4%) respondents confirmed using at least 1 drain, while 43 (40.6%) placed 2 IPDs. Only 13 respondents (12.3%) declared a change in IPD strategy in patients at high risk of clinically relevant postoperative pancreatic fistula (CR-POPF), while 9 (9.4%) respondents changed their strategy in low-risk POPF situations. Thirty-five (35.5%) respondents declared they would remove the IPD within the third postoperative day (POD) in the absence of CR-POPF suspicion. The median omission regret, which proved to be the wrong decision, was 80 (50–100, IQR). The median regret due to the commission of IPD, which turned out to be useless, was 2.5 (1–20, IQR). The CR-POPF probability threshold at which drainage omission was the less regrettable choice was 7% (1–35, IQR). The threshold to perceive drain omission as the least regrettable choice was higher in female surgeons (P < 0.001), in surgeons who modulated the strategies based on the risk of CR-POPF, and in high volume centers (p = 0.039). The threshold was lower in surgeons who performed minimally invasive distal pancreatectomy (P < 0.001), adopted a closed system (P < 0.001), placed two IPDs (P < 0.001), or perceived the IPD as important to prevent reintervention (p = 0.047). Drain management after DP remains very heterogeneous among surgeons. The regret model suggested that IPD omission could be performed in low-risk patients (7% of CR-POPF), leading to low regret in the case of the wrong decision, making it an acceptable clinical decision.