Background: Limited data are available that examine hospital readmission outcomes of sliding scale compared to basal-bolus insulin in indigent and insulin-naive patients. Objective: To evaluate hospital readmission outcomes in patients who are insulin naive with type 2 diabetes mellitus who are initiated on either sliding scale or basal-bolus insulin upon hospital discharge. Methods: A retrospective chart review was conducted of adult patients with a history of type 2 diabetes mellitus, who were insulin naive, had a hemoglobin A1c (HbA1c) 10% or greater, and were discharged with a prescription for sliding scale or basal-bolus insulin from January 2015 to July 2018. The primary objective measured all-cause 30-day hospital readmissions. The secondary objectives measured diabetes-related 30-day hospital readmissions and HbA1c change after 3 months of initial hospital admission. Data were analyzed using descriptive statistics, χ2 test, paired sample t test, and logistic regression. Results: Forty-one patients were prescribed sliding scale insulin and 105 patients were prescribed basal-bolus insulin. The majority were male (60%), spoke English (84%), were self-pay (39%), and had a mean age of 51 ± 10.2 years, initial HbA1c of 13% ± 1.9%, and LACE+ score of 51 ± 15.6 upon discharge. All-cause 30-day hospital readmissions occurred in 14.6% of sliding scale and 6.7% of basal-bolus insulin groups (odds ratio [OR]: 2.40, 95% confidence interval [CI]: 0.75-7.63). Hyperglycemia occurred in 7.3% of sliding scale and 0.9% of basal-bolus insulin groups. Mean HbA1c difference for basal-bolus and sliding scale insulin was 3.3 ± 3.1 and 2.9 ± 2.7, respectively ( P = 0.459). Conclusion: There was no significant difference in all-cause 30-day hospital readmissions comparing sliding scale to basal-bolus insulin.