Importance Gender-affirming orchiectomy may be performed in isolation, as a bridge to vaginoplasty, or concurrently with vaginoplasty for transgender and nonbinary persons, although there is a paucity of data on immediate postoperative outcomes on the various procedural approaches.Objective The aim of the study is to compare 30-day surgical outcomes after gender-affirming orchiectomy and vaginoplasty as separate and isolated procedures. Study Design This was a retrospective cohort study of patients in the American College of Surgeons National Surgical Quality Improvement Program database to compare surgical outcomes of orchiectomy alone and vaginoplasty alone to concurrent orchiectomy with vaginoplasty using bivariate and adjusted multivariable regression statistics. Results Concurrent orchiectomy and vaginoplasty were associated with greater 30-day surgical complications compared with orchiectomy alone (15.4% vs 2.9%, P < 0.01) and similar odds of 30-day surgical complications compared with vaginoplasty alone (15.4% vs 11.1%, P = 0.15). On multivariable logistic regression analysis, compared with orchiectomy alone, concurrent orchiectomy and vaginoplasty were associated with higher increased odds of 30-day surgical complications (adjusted odds ratio, 6.48; 95% confidence interval, 2.83-14.86) as well as vaginoplasty alone (adjusted odds ratio 4.30; 95% confidence interval, 1.85-10.00). Conclusions This study highlights the perioperative outcomes for isolated versus concurrent gender-affirming orchiectomy and vaginoplasty, demonstrating lower morbidity for orchiectomy alone and similar morbidity for vaginoplasty alone when compared with concurrent procedures. These data will aid health care providers in preoperative counseling and surgical planning for gender-affirming genital surgery, particularly for patients considering concurrent versus staged orchiectomy and vaginoplasty.