The authors wanted to analyse teachers and specialist councillors and compare their levels of stress, mental wellbeing, their occupational tasks, the assessment of the support received and the additional help that they expected whilst working online during the first wave of SARS-CoV-2 amidst the transformation of the educational system in Poland. Data were collected using a questionnaire, PSS 10, and the scale based on GHQ12 and GH30. The findings highlighted that the pandemic situation and the need to work remotely most likely increased the stress levels and thus lowered the mental wellbeing of the teachers and specialists surveyed, although the results indicate that stage III teachers may have experienced more difficulties, and specialists working in counselling fewer difficulties. The research showed the inadequacy of the support perceived by the teachers in relation to the difficulties experienced during remote work. Specialists provided support primarily to other specialists, but not to teachers.