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BACKGROUND: Identifying predictors of chronic heart failure is an essential preventive step in patients with pre–heart failure. AIM: This study aimed to identify predictors of chronic heart failure development in outpatients with hypertension and pre–heart failure. METHODS: A single-center study included 356 outpatients with hypertension and pre–heart failure. The mean age was 62.65 ± 10.59 years; 128 (36%) participants were men. The patients received drug therapy for hypertension, with treatment adjustment after 1 and 3 months and subsequently annually for 3 years. Later on, outcomes defined as the development of chronic heart failure were evaluated. Multiple binary logistic regression analysis was used to identify predictors of chronic heart failure onset. RESULTS: Over a 3-year period (2022–2025), chronic heart failure with preserved ejection fraction developed in 8.7% of patients with hypertension and pre–heart failure. Analysis of risk factors showed that patients who developed chronic heart failure were older (66.37 ± 9.55 years; p 0.001), had a longer duration of hypertension (17.85 ± 10.43 years; p 0.001), higher body mass index (29.41 ± 4.85 kg/m2; p = 0.002), and a lower glomerular filtration rate (73.23 ± 18.19 mL/min/1.73 m2; p 0.001). In this group, paroxysmal (p 0.001) and persistent atrial fibrillation (p 0.001), as well as type 2 diabetes mellitus (p 0.001), were observed more frequently. In these patients, more pronounced structural and functional cardiac changes were already present at enrollment into the study, namely, indexed left atrial volume (47.93 ± 14.85 vs 33.68 ± 5.57 mL/m2; p 0.001), indexed myocardial mass (104.18 ± 29.34 vs 92.55 ± 19.36 g/m2; p = 0.045), maximum pulmonary vein diameter (21.23 ± 2.24 vs 17.34 ± 1.64 mm; p 0.001), and minimum pulmonary vein diameter (11.09 ± 2.42 vs 7.36 ± 1.53 mm; p 0.001). The predictors associated with the onset of chronic heart failure after 3 years in patients with hypertension included maximum pulmonary vein diameter, left atrial volume, age, body mass index, and the presence of atrial fibrillation. CONCLUSION: Within 3 years, chronic heart failure with preserved ejection fraction developed in 8.7% of patients with pre–heart failure. Predictors of its development in patients with hypertension included maximum pulmonary vein diameter, left atrial volume, age, body mass index, and the presence of atrial fibrillation.