Ductal carcinoma in situ (DCIS) accounts for approximately 30% of new breast cancer diagnoses. However, our understanding of how normal breast tissue evolves into DCIS and invasive cancers remains insufficient. Further, conclusions regarding the mechanisms of disease progression in terms of histopathology, genetics, and radiology are often conflicting and have implications for treatment planning. Moreover, the increase in DCIS diagnoses since the adoption of organized breast cancer screening programs has raised concerns about overdiagnosis and subsequent overtreatment. Active monitoring, a nonsurgical management strategy for DCIS, avoids surgery in favor of close imaging follow-up to de-escalate therapy and provides more treatment options. However, the two major challenges in active monitoring are identifying occult invasive cancer and patients at risk of invasive cancer progression. Subsequently, four prospective active monitoring trials are ongoing to determine the feasibility of active monitoring and refine the patient eligibility criteria and follow-up intervals. Radiologists play a major role in determining eligibility for active monitoring and reviewing surveillance images for disease progression. Trial results published over the next few years would support a new era of multidisciplinary DCIS care.