Objective. The aim of the study was to evaluate perceived stress and coping strategies in subjects with hypertension, according to the presence of insomnia symptoms, using a set of variables that include anxiety and depressive symptoms evaluation. Methods. 371 hypertensive patients at their first visit at the Hypertension Outpatient Unit were enrolled. Perceived Stress Scale (PSS), Brief-COPE, Insomnia Severity Index (ISI), Beck Depression Inventory (BDI), Self-rating Anxiety Scale (SAS), and State-Trait Anxiety Inventory (STAI) were administered. Patients with other sleep disorders or with incomplete data (n=41) were excluded. Results. Data from 330 hypertensive patients were analyzed (males 51%, mean age 57±13 years). Patients with insomnia symptoms (n=70, 21%) were older (p=0.02), more frequently females (p=0.01) and presented higher PSS (p<.001), BDI (p<.0001), SAS (p=.0003) and STAI (p<.0001) scores than patients without symptoms of insomnia. In a linear regression trait anxiety (p<.0001) and depressive symptoms (p<.05) were independent predictors of high PSS. Patients with insomnia symptoms showed lower scores of coping strategies such as positive reframing (p=.03), emotional support (p=.04) and an increased score in behavioral disengagement (p=.03). Trait anxiety and insomnia severity were independent predictors of less effective coping strategies. Conclusions. Hypertensive patients with insomnia symptoms show higher perceived stress and less effective coping strategies than non insomniacs; psychological factors such as trait anxiety and depressive symptoms may play a modulating role in these relationships. Prevention and treatment of insomnia symptoms and of psychological factors should receive high attention in patients with hypertension.