While many factors influence decisions related to the timing between mastectomy and flap-based breast reconstruction, there is limited literature comparing postoperative complications between immediate (IBR), delayed immediate (DIBR), and delayed (DBR) reconstruction modalities. Using the National Surgical Quality Improvement Program (NSQIP), we sought to compare postoperative complication rates of each timing modality. The NSQIP 2010-2020 database was queried for patients who underwent free flap breast reconstruction. Cases were categorized to include mastectomy performed concurrently with a free flap reconstruction, removal of a tissue expander with free flap reconstruction, and free flap reconstruction alone which are defined as IBR, DIBR, and DBR, respectively. The frequency of postoperative outcomes including surgical site infection (SSI), wound dehiscence, intraoperative transfusion, deep venous thrombosis (DVT), and return to operating room (OR) was assessed. Overall complication rates, hospital length of stay (LOS), and operative time were analyzed. Multivariable regression analysis controlling for age, race, BMI, diabetes, hypertension, ASA class, and laterality was performed. A total of 7,907 cases that underwent IBR, DIBR (n = 976), and DBR reconstruction (n = 6,713) were identified. No statistical difference in occurrence of SSIs, wound dehiscence, or DVT was identified. DIBR (9%) and DBR (11.9%) were associated with less occurrences of reoperation than IBR (13.2%, p < 0.001). Univariate and multivariate regression analysis demonstrated that DIBR and DBR were associated with a lower odds of complications and shorter operation time versus IBR. No statistically significant differences between DIBR and DBR in surgical complications, LOS, and operative time were identified. Awareness of overall complication rates associated with each reconstructive timing modality can be used to help guide physicians when discussing reconstructive options. Our data suggests that DIBR and DBR are associated with less overall complications than IBR. Physicians should continue to consider patients' unique circumstances when deciding upon which timing modality is appropriate.