Introduction: Small Bowel Obstruction (SBO) accounts for 15% of emergency department (ED) admissions. While conservative management is recommended, surgery becomes necessary when strangulation is suspected. Identifying which patients need surgery remains a challenge, as traditional imaging lacks sufficient sensitivity and specificity. This study aimed to explore radiomic features to identify potential predictors of strangulation. Methods: This retrospective study included patients admitted to a tertiary referral hospital ED between 2019 and 2023, diagnosed with Adhesion Small Bowel Obstruction (aSBO) via contrast-enhanced abdominal CT scans. Two patient groups were examined: those who underwent surgery with bowel resection and ischemic changes confirmed histologically (operative management—OM) and those successfully treated with conservative management (CM). All CT scans were reviewed blindly by a general surgeon and an experienced radiologist. Pre-obstructive loop segmentation was performed using 3D Slicer software, with slice-by-slice contouring of intestinal borders on images of suspected strangulated bowel. Radiomic features were extracted, followed by univariate and multivariate regression analysis. Results: A total of 55 patients were included: 27 CM and 28 OM. Significant differences emerged in GLCM (Gray Level Co-occurrence Matrix), GLDM (Gray Level Dependence Matrix), GLRLM (Gray Level Run Length Matrix), and GLSZM (Gray Level Size Zone Matrix), particularly involving entropy and uniformity. These metrics reflect subtle variations in gray levels not visible to the naked eye. Conclusions: Differences in entropy, uniformity, and energy align with imaging and histopathological findings, supporting the development of radiomic models and future AI-based prediction tools.