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Objectives: The current European crisis in human resources in health has opened the debate about working conditions and fair wages. This is the case with Resident doctors, which have faced challenges throughout Europe. In Portugal, they account for about a third of the doctors in the Portuguese National Health Service. No studies to date objectively demonstrate the working conditions and responsibilities undertaken. This study aims to quantify the residents' workload and working conditions. Methods: Observational, retrospective cross-sectional study which involved a survey on the clinical and training activity of Portuguese residents, actively working in September 2020. The survey was distributed through e-mail to residents' representatives and directly to those affiliated with the Independent Union of Portuguese Doctors. The descriptive analysis assessed current workload, and logistic regression models analyzed associations with geographical location and residency seniority. Results: There were a total of 2,012 participants (19.6% of invited residents). Of the residents giving consultations, 85.3% do so with full autonomy. In the emergency department, 32.1% of the residents work 24 h shifts and 25.1% work shifts without a specialist doctor present. Regarding medical training, 40.8% invest over EUR 1,500 annually. Autonomy in consultations was associated with being a Family Medicine resident (OR 4.219, p < 0.001), being a senior resident (OR 5.143, p < 0.001), and working in the Center (OR 1.685, p = 0.009) and South regions (OR 2.172, p < 0.001). Seniority was also associated with investing over EUR 1,500 in training annually (OR 1.235, p = 0.021). Conclusion: Residents work far more than the contracted 40 h week, often on an unpaid basis. They present a high degree of autonomy in their practice, make a very significant personal and financial investment in medical training, with almost no time dedicated to studying during working hours. There is a need to provide better working conditions for health professionals, including residents, for the sake of the sustainability of health systems across Europe. [ABSTRACT FROM AUTHOR]