This study aimed to identify the radiological CT findings that are significantly correlated with the outcome of conservative management with oral water-soluble contrast medium in patients presenting with Adhesive Small Bowel Obstruction (ASBO) to the Emergency Room. In this retrospective single-center study, we considered all consecutive patients admitted to the ER from February 2019 to February 2023 for ASBO with an available contrast-enhanced CT scan performed at diagnosis and treated with conservative management. The investigated CT findings were type and location of transition zone, ASBO degree, fat notch sign, beak sign, small bowel feces sign, presence of peritoneal free fluidand pneumatosis intestinalis. Radiological parameters were analyzed using univariable and multivariable logistic regression to test the significant association between the CT parameters and the target. Among the 106 included patients (median age 74.5years), conservative treatment was effective in 59 (55.7%) and failed in 47 (44.3%), needing delayed surgery. In the failure group, there was a higher prevalence of patients who had previous ASBO episodes (p = 0.03), a greater proportion of females (p = 0.04) and a longer hospital stay (p < 0.001). At multivariable analysis, two CT findings were significantly correlated with failure of conservative treatment: fat notch sign (OR = 2.95; p = 0.04) and beak sign (OR = 3.42; p = 0.04). Two radiological signs correlate with failure of non-operative management in ASBO, suggesting their importance in surgical decision-making. Patients presenting with these signs are at higher risk of unsuccessful conservative treatment and may require undelayed surgical intervention.