Because of the coronavirus disease 2019 (COVID-19) emergency, on March 9, 2020 Italy went in lock-down imposing the closure of non-urgent outpatient clinics devoted to care of chronic, severe, inflammatory skin diseases that require periodic follow-up. In this emergency situation, due to the lack of a teledermatology platform and in order not to leave our vulnerable high-need patients without proper follow-up, we started a teledermatologic service in smartworking using phone calls and emails. The total number of patients scheduled was 195; in 12 cases, we were not able to talk to the patients. Remote monitoring was performed in 183 patients (126 moderate to severe psoriasis, 10 severe acne, 11 severe atopic dermatitis, 11 hidradenitis suppurativa, 9 blistering autoimmune diseases, and 16 other autoimmune skin diseases). During remote-visits, several interventions were conducted: triage for COVID-19 suspected symptoms, email check of clinical pictures and of laboratory examinations, advices for topical and systemic therapy continuation or discontinuation/switch and reschedule of next appointment. Only five patients required personal office visit (2.7%), reducing consistently the number of face-to face visits. Our real-life experience shows that remote monitoring was effective in preventing unnecessary worsening of severe chronic skin diseases and poor outcomes due to withdrawal of current therapy.