BACKGROUND: The coronavirus disease 2019 (COVID-19) pandemic spurred a tremendous increase in the adoption and use of remote patient monitoring (RPM) for hypertension (HTN) management. However, limited evidence exists on the associations between frequency of utilization and uncontrolled blood pressure (BP). OBJECTIVES: The present study comprehensively explores the associations between RPM use frequency and uncontrolled BP among a metropolitan-dwelling sample of hypertensive patients. METHODS: Of 2,920 participants from a single urban health system, we employed a range of analytical perspectives to evaluate the RPM utilization-uncontrolled BP relationship across widely used engagement metrics: Frequency of BP transmission, digitally enabled clinician interactions, patient portal interactions, and a composite measure of utilization. Our dichotomized primary and secondary endpoints were BP >140/90 mm Hg and BP >130/80 mm Hg. RESULTS: Fifty-nine percent of participants were females (59%), one-third (37%) were ≥65 years old, and Hispanic patients were most represented (39%). Our primary uncontrolled BP endpoint demonstrated strong adjusted associations with suboptimal RPM use across dichotomized measures: Low BP transmission (odds ratio [OR]: 2.02, 95% confidence interval [CI]: 1.41-2.96), low clinician interactions (OR: 1.83, 95% CI: 1.43-2.36), low patient portal interactions (OR: 1.83, 95% 1.46-2.30), and low overall engagement (OR: 3.50, 95% 2.77-4.46). Our causal evaluations mirrored these findings, showing moderate causal associations after comprehensive adjustment for confounding. Assessments using other data types, such as continuous and quartiles, showed significant associations and an apparent dose-response relationship, though not at a similar magnitude. CONCLUSION: We observed strong associations between low RPM utilization and uncontrolled BP, with promising implications for patients with collectively high RPM use. These findings highlight the need to strengthen digital inclusion initiatives to improve RPM uptake and support existing efforts aimed at developing RPM clinical practice guidelines and expanding RPM reimbursement policies. Further research is warranted across diverse utilization components to better understand the linkages between engagement frequency and improved clinical outcomes.