The research aims to analyze the advancement of digital competencies in educators within the framework of a continuing professional education program in the field of online learning and identify possible directions for updating distance learning for educators. During the empirical research, the authors diagnosed the formation of digital competencies among educators in the cities of the Siberian Federal District (Russia). The authors used various methods to study the parameters, including testing, surveys, focus groups, and phenomenological methods for characterizing digital competence. The authors developed the following criteria for assessing the digital competence of educators: cognitive-semantic criterion, communicative criterion, and activity criterion. Additionally, the authors developed blocks of indicators for each criterion. Three levels of digital competence assessment were identified: integrative, basic, and elementary. First, statistical analysis proved the reliability of the increase in indicators for the cognitive-semantic criterion (CSC): ICC1(t =  −31.336; p < 0.001), ICC2(t =  −35.067; p < 0.001), and ICC3(t =  −41.024; p < 0.001). Second, the analysis proved the reliability of the indicators of the communicative criterion (CC): CC1(t =  −23.023; p < 0.001) and CC2(t =  −19.21; p < 0.001). Third, the reliability of the activity criterion (AC) was also proven: AC1(t =  −33.335; p < 0.001), AC2(t =  −36.23; p < 0.001), AC3(t =  −15.772; p < 0.001), AC4(t =  −26.691; p < 0.001), and AC5(t =  −19.901; p < 0.001). The assessment of digital competencies revealed the peculiarities of their formation: multidimensionality, sensitivity to socio-cultural context, cyclicity in development, and dependence on the motivational and personal structure of the educator.