Background: Telehealth has the potential to improve chronic disease management and outcomes, but data regarding direct benefit of telehealth in patients with heart failure (HF) have been mixed. The objective of this study was to determine whether the Health Buddy Program (HBP) (Bosch Healthcare, Palo Alto, CA), a content-driven telehealth system coupled with care management, is associated with improved outcomes in Medicare beneficiaries with HF. Materials and Methods: This was a retrospective cohort study of 623 Medicare beneficiaries with HF offered HBP enrollment compared with a propensity score-matched control group of Medicare beneficiaries with HF from the Medicare 5% sample. Associations between availability of the HBP and all-cause mortality, hospitalization, hospital days, and emergency department visits were evaluated. Results: Beneficiaries offered enrollment in the HBP had 24.9% lower risk-adjusted all-cause mortality over 3 years of follow-up (hazard ratio [HR] = 0.75; 95% confidence interval [CI], 0.63-0.89; p = 0.001). Patients who used the HBP at least once (36.9%) had 57.2% lower mortality compared with matched controls (HR = 0.43; 95% CI, 0.31-0.60; p < 0.001), whereas patients who did not use the HBP had no significant difference in survival (HR = 0.96; 95% CI, 0.78-1.19; p = 0.69). Patients offered the HBP also had fewer hospital admissions following enrollment (D = -0.05 admissions/quarter; p = 0.011), which was primarily observed in patients who used the HBP at least once (D = -0.10 admissions/quarter; p < 0.001). Conclusions: The HBP, a content-driven telehealth system coupled with care