Although patients diagnosed with ductal carcinoma In Situ (DCIS) enjoy a favorable prognosis, recurrence after definitive management does occur in a subset of these patients. Factors influencing the development of recurrence remain poorly understood. A retrospective chart review of 205 consecutive patients who presented to an academic breast center with DCIS from 2000 to 2003 was conducted under an Institutional Review Board-approved protocol. With a median follow-up of 8.5 years, 14 (6.8%) of the 205 patients who presented with DCIS between 2000 and 2003 had a recurrence of their DCIS. The median age of all patients at the time of diagnosis of their initial DCIS was 55.5 years (range, 35.8 to 88.9 years). Patients who experienced tumor recurrence were more likely to have Grade 3 DCIS on initial diagnosis compared with patients without recurrence (72.7 vs 35.4%, P = 0.032). The odds ratio of tumor recurrence for high-grade compared with low-grade DCIS was 4.39. Patient age, race, tumor size, tumor histologic subtype, or histopathologic features was not associated with recurrence. Patients with high-grade DCIS are more likely to recur than patients with low-grade DCIS, and this seems to be more predictive of recurrence than other clinicopathologic markers.