Postoperative pancreatic fistula (POPF) is a serious complication after pancreatic resection, increasing morbidity, hospital stay, and healthcare costs. We present an automatic, end-to-end deep learning pipeline-from pancreatic segmentation to classification-for preoperative POPF risk estimation and stratification using preoperative CT scans. A data set with auto-segmented pancreas volumes and surgical outcomes was used to evaluate multiple architectures, including a custom lightweight 3D CNN baseline (CNN3D), R(2+1)D ResNet-18, and ResNet-MC3-18 models. Evaluation across multiple 3D architectures demonstrated promising predictive performance. This approach offers a clinically valuable tool and a methodological benchmark for pancreas-specific CT classification, supporting improved preoperative decision-making in pancreatic surgery.