Background/Objectives: The management of acute uncomplicated diverticulitis (AUD) has shifted towards outpatient care in the last decade, challenging the traditional inpatient approach. We aimed to analyze the safety and feasibility of a structured outpatient treatment pathway for AUD in a tertiary hospital. Methods: We conducted a retrospective observational cohort analysis of patients who underwent outpatient management for AUD at the Geneva University Hospitals from 2019 to 2021. Patient demographics, selection criteria, treatment protocols, and outcomes were analyzed. Results: Two-hundred and twenty patients were included in the outpatient cohort. Four patients (1.8%) required hospitalization due to the failure of outpatient management, whereas the majority of patients (116 patients, 98.2%) experienced a successful resolution of their symptoms without hospitalization. In a univariate analysis, factors associated with treatment failure included elevated white blood cell counts at admission (14 G/l vs. 10.6 G/l, p = 0.049) and the first follow-up appointment, (10.7 G/l vs. 7.4 G/l, p = 0.011) and the presence of free air on their CT scan (25% vs. 2,3%, p = 0.033). In a multivariate analysis, the presence of free air was the only identified risk factor for unsuccessful outpatient management (p = 0.05). We observed high rates of follow-up compliance (99.1%). Conclusion: Under the condition of a warranted outpatient follow-up appointment and with adequate selection criteria, outpatient management appears to be an effective approach for most patients with AUD, emphasizing the importance of tailored therapeutic interventions and vigilant clinical assessments for optimal outcomes.