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(1) Background. During the COVID-19 pandemic, healthcare professionals faced psychological and social challenges in addition to a sharp increase in workload. The aim of this work was to reveal how healthcare and pharmacy workers assessed their wellbeing and the methods of coping they employed to overcome stress during quarantine. (2) Methods. The mixed-method study was conducted between August and October 2020, integrating quantitative (n = 967) and qualitative (n = 27) strategies. Doctors, nurses, healthcare administrative staff, pharmacy specialists, and other employees of the healthcare system were interviewed retrospectively about their experiences during and following lockdown (March-June 2020). (3) Results. Overall, 38.7% of the respondents reported a decrease in psychological wellbeing, while 23.4% of the respondents reported a decrease in physical wellbeing during quarantine. The …