The authors of the article have conducted a sociological study of the problem of confidence in schoolteachers in the Moscow region in autumn of 2019. They have interviewed teachers, students and their parents in the suburbs of Ramenskoye and the city of Orekhovo-Zuevo (these cities are located at different distances from Moscow), which has made it possible to see more clearly the socio-cultural specificity of the studied problem. In the article, the authors pay particular attention to the factors that affect mutual understanding between all the actors of the learning process. The authors conclude that the problem of confidence in schoolteachers is becoming more urgent, and the need for its systematic monitoring in schools appears. Considering the spread of distance learning, the authors of the article suggest that schoolteachers will face additional difficulties in building trusting relationships with students and their parents. The experience of the study, presented in the article, will be useful for finding solutions to the problem of confidence between all the actors of the learning process in changing conditions.