OBJECTIVE Pregnancy has been associated with development and progression of diabetic retinopathy (DR), but incidence of DR remains unclear. We assessed DR progression rate and its predictors during pregnancies in patients with type 1 diabetes. RESEARCH DESIGN AND METHODS We report the retrospective data from pregnancies in patients with type 1 diabetes followed in Lille, France (1997–2015). Eye examination was performed every 3 months or every month in case of severe nonproliferative retinopathy or progression. Progression was defined by DR degradation (≥1 stage of the Early Treatment Diabetic Retinopathy Study [ETDRS] classification); it included DR development and worsening in patients without and with prepregnancy DR, respectively. RESULTS A total of 499 pregnancies in 375 patients were included; prepregnancy retinopathy was present in 30.3%. Progression, development, and worsening rates were 21.8%, 24.4% of those without retinopathy, and 15.9% of those with retinopathy, respectively. Development of sight-threatening retinopathy was rare. Progression mainly occurred in early or midpregnancy. Elevated prepregnancy HbA1c and duration of diabetes ≥10 years were predictors of DR progression. Among pregnancies with prepregnancy DR, continuous subcutaneous insulin infusion (CSII) tended to decrease the risk of DR progression. Among CSII-treated patients, those with prepregnancy DR had a significantly decreased risk of DR progression. Among the 270 pregnancies of women with any DR during pregnancy who returned for a postpartum ophthalmologic examination, the rate of progression was only 4.1% and the rate of regression was 9.3%. CONCLUSIONS This study provides epidemiologic data on progression of retinopathy during pregnancy and will be useful for future guidelines for retinopathy screening.