Background: National Comprehensive Cancer Network (NCCN) guidelines recommend systemic imaging for local-regional recurrence after breast cancer treatment. Limited data exists to support this recommendation. Our objective was to determine the rate of synchronous distant recurrence at the time of local-regional recurrence in high-risk patients and identify clinical factors associated with increased risk of synchronous metastases. Methods: A stage-stratified random sample of 10,333 patients diagnosed with Stage II-III breast cancer in 2006-2007 was selected from the National Cancer Database for additional medical record abstraction of imaging and recurrence. Patients who experienced local-regional recurrence within five years of diagnosis were identified. Synchronous presentation of distant metastases (within 30 days) was determined. Patient factors associated with synchronous presentation were assessed with logistic regression. Results: Of 10,333 patients, 442 (4.3%) developed a local-regional recurrence. Synchronous distant metastases were identified in 27.1% (n = 120). These metastases were most commonly detected on cross-sectional imaging (55.8%) or patient-reported symptoms (31.7%). The proportion of synchronous metastases varied by local-regional recurrence type (p = 0.008) and was highest for women with lymph node (35.6%), followed by chest wall (31.0%), and in-breast (15.9%) recurrence, and for patients with stage III (37.4%) versus stage II (20.1%) disease (p = 0.009). Age, molecular tumor subtype, and race were not associated with the likelihood of synchronous metastases. Conclusions: Approximately 27% of high-risk patients with local-regional recurrence have synchronous distant metastases. This data provides support for the current NCCN recommendation for systemic imaging in this setting, particularly for patients with lymph node or chest wall recurrences.