Purpose: To estimate the upstaging risk of symptomatic ductal carcinoma in situ (DCIS) to invasive disease and to identify features related to upstaging risk. Materials and methods: This retrospective investigation includes symptomatic women with DCIS at core needle biopsy from January 2007 to December 2016 at a large academic institution. Patient characteristics, findings at imaging, core needle biopsy histopathology results, and final surgical histopathology results were retrieved from the medical records. Using standard statistical tests, patient, imaging, and pathology features were compared between DCIS cases that were upstaged to invasive disease at surgery versus cases that were not upstaged. Results: From 2007 to 2016, fewer than 5% (63/1399) of women diagnosed with DCIS presented with symptoms. Therefore, 63 women (mean age, 51; range, 27-88 years) comprised the study cohort. 84.1% (n = 53) presented with an area of clinical concern, and 15.9% (n = 10) presented with pathologic nipple discharge. The most common finding at mammography was calcifications with or without an associated asymmetry or mass (74.1%, 40/54). The upstaging rate of symptomatic DCIS to invasive disease was 34.9% (22/63). Imaging modality used for biopsy was associated with higher upstaging risk, with cases that were biopsied under MRI guidance accounting for 22.7% of upstaged cases versus 4.9% of non-upstaged cases (p = 0.03). Conclusions: Women with DCIS uncommonly present with symptoms, and the upstaging rate of symptomatic DCIS is high at nearly 35%. Biopsy modality type of MRI is associated with higher upstaging risk.