There is no guideline regarding whether patients treated with intravenous corticosteroids for acute severe ulcerative colitis (ASUC) should be monitored in the hospital after transitioning to oral steroids. Our study aimed to: (1) compare rates of oral steroid transition failure and 30-day readmission between ASUC hospitalizations with extended inpatient monitoring compared to accelerated inpatient monitoring, and (2) identify predictors of oral steroid transition failure. A retrospective cohort study of ulcerative colitis (UC) related admissions at UCSF from 2014 to 2022 was conducted comparing rates of steroid transition failures in extended inpatient monitoring (≥ 24h on oral steroids prior to discharge) to accelerated inpatient monitoring (< 24h on oral steroids). Steroid transition failure was defined as worsening colitis activity with the need to return to IV steroids or undergo colectomy. Data analysis incorporated demographics, disease features, and treatment history. Transition failures from intravenous to oral corticosteroids occurred in 8% of all UC-related admissions. There was a significant difference in transition failure observed between the extended and accelerated monitoring groups, 13 vs 3% (p = 0.03), respectively, with 83.3% of total transition failures occurring within the extended monitoring group. The 30-day readmission rate was 6% in each group (p = 0.93). No significant predictors of transition failures were identified. Transition failures from IV to oral steroids are uncommon in ASUC hospitalizations. Transition failures were more likely to occur with extended monitoring, suggesting potential predictors and/or patient selection bias within this group. Further studies are needed to investigate the parameters driving clinician decision-making regarding oral steroid transitioning.