The term ductal carcinoma in situ (DCIS) encompasses a heterogeneous group of lesions that differ in their clinical behavior. Clinical factors such as symptomatic presentation and young age are associated with an increased risk of local recurrence in patients with DCIS managed with breast-conserving therapy. Treatment factors such as wider surgical margins, the use of radiation therapy, and the use of tamoxifen reduce the local recurrence risk. Pathological characteristics such as larger lesion size, high nuclear grade, comedo necrosis, and involved margins are associated with an increased risk of local recurrence in many studies. However, there are complex interactions between these pathological risk factors and other parameters such as treatment and length of follow-up. In fact, the magnitude of the effect of these pathological features on local recurrence risk is modified by these other factors. Analysis of genetic and molecular alterations as well as study of the microenvironment associated with DCIS are important avenues of research that may provide new insights into DCIS recurrence and progression risk, and this in turn may lead to new strategies for treatment and prevention.