Introduction: Homeless Veterans are vulnerable to poor care transitions, yet little research has examined their risk of readmission following inpatient surgery. This study investigates the predictors of surgical readmission among homeless relative to housed Veteran patients. Methods: Inpatient general, vascular, and orthopedic surgeries occurring in the Veterans Health Administration from 2008 to 2014 were identified. Administrative International Classification of Diseases, Ninth Revision, Clinical Modification codes and Veterans Health Administration clinic stops were used to identify homeless patients. Bivariate analyses examined characteristics and predictors of readmission among homeless patients. Multivariate logistic models were used to estimate the association between homeless experience and housed patients with readmission following surgery. Results: Our study included 232,373 surgeries: 43% orthopedic, 39% general, and 18% vascular with 5068 performed on homeless patients. Homeless individuals were younger (56 vs. 64 y, P<0.01), more likely to have a psychiatric comorbidities (51.3% vs. 19.4%, P<0.01) and less likely to have other medical comorbidities such as hypertension (57.1% vs. 70.8%, P<0.01). Homeless individuals were more likely to be readmitted [odds ratio (OR), 1.43; confidence interval (CI), 1.30-1.56; P<0.001]. Discharge destination other than community (OR, 0.57; CI, 0.44-0.74; P<0.001), recent alcohol abuse (OR, 1.45; CI, 1.15-1.84; P<0.01), and elevated American Society Anesthesiologists classification (OR, 1.86; CI, 1.30-2.68; P<0.01) were significant risk factors associated with readmissions within the homeless cohort. Conclusions: Readmissions are higher in homeless individuals discharged to the community after surgery. Judicious use of postoperative nursing or residential rehabilitation programs may be effective in reducing readmission and improving care transitions among these vulnerable Veterans. Relative costs and benefits of alternatives to community discharge merit investigation.