Half of the individuals with type 1 diabetes (T1DM) may present Vitamin D (VD) deficiency. There is little known about factors determining a decision on VD supplementation. The study aimed to determine the factors affecting vitamin D supplementation in people with T1DM. A cross-sectional survey study using the authors’ questionnaire paper and its digital version was performed. The questions involved data on the basic characteristics of the respondent, medical history, VD supplementation status, influence of the social environment, self-education, and the most important personal motivator for VD supplement use. Multivariate logistic regression analysis was performed. We collected a total of n = 184 papers and n = 550 digital complete surveys. From 734 total respondents, 62.0% declared VD supplementation. The main personal rationale for VD supplementation were recommendation of medical specialist 172 (37.8%) and self-education 135 (29.7%). The main reasons for non-supplementation of VD were lack of knowledge about VD 159 (57.0%) and lack of motivation 77 (27.6%). VD supplementation was independently associated with a family doctor (odds ratio (OR), 95% confidence interval (CI): 4.67, 2.32–9.40) or medical specialist recommendation (16.20, 9.57–27.43), and self-education (5.97, 3.90–9.13). Most Polish individuals with T1DM use VD supplements, and the decision is related to physicians’ recommendations and self-education.