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Obstructive sleep apnea (OSA) is associated with increased cardiovascular risk, sedentarism, depression, anxiety and impaired quality of life. The long-term effectiveness of positive airway pressure (PAP) is insufficiently studied and limited by poor patient compliance. The aim of this pilot prospective cohort study was to evaluate long-term adherence in overweight patients with moderate–severe OSA and hypertension and to analyze changes in weight, sleepiness and quality of life. We performed a prospective study that included overweight patients with moderate–severe OSA and hypertension who had not undergone previous PAP therapy. All subjects received a standard physical examination, education regarding lifestyle changes and free PAP therapy for 2 months. After five years, the patients were invited to participate in a telephone-based interview regarding PAP compliance and completed standard questionnaires assessing adherence to medication, physical activity, diet, anxiety and quality of life (QoL). Only 39.58% of the patients were adherent to PAP 5 years (58.42 ± 3.70 months) after being diagnosed with moderate–severe OSA. Long-term PAP use results in sustained weight loss; improved blood pressure control, sleepiness and QOL; and lower anxiety and depression scores. PAP compliance was not associated with a higher level of daily physical activity or a healthier diet.