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Abstract Introduction Virtual maternity solutions vary widely in clinical depth, and their association with physiological outcomes in high‐risk populations remains understudied. We evaluated the association between the duration of engagement in a multispecialty virtual maternity program and neonatal outcomes among a medically complex population. Methods We conducted a retrospective cohort study using administrative claims from six Medicaid‐managed care plans across six US states (January 2024–April 2025). We compared outcomes of patients enrolled in a virtual program, integrating remote patient monitoring, multispecialty care, and social support, against propensity‐weighted comparators receiving standard care. The population exhibited a high comorbidity burden, including 36% rates of hypertension and 50% of obesity. The primary exposure was engagement duration (≥1, ≥2, and ≥3 months). Primary outcomes were preterm birth, neonatal intensive care unit (NICU) admission, and NICU length of stay (LOS), estimated using doubly robust modified Poisson regression with inverse probability of treatment weighting (IPTW). Results The analysis of longer engagement (≥3 months) included 3785 treated patients and 38,180 weighted comparators. Engagement of ≥3 months was associated with a 24.4% reduction in the adjusted relative risk of preterm birth (95% CI, −32.5% to −15.4%; p < 0.001), decreasing the absolute rate from 11.6% to 8.8%. This cohort also experienced a 12.5% reduction in NICU admissions (95% CI, −21.0% to −3.2%; p = 0.01) and a 26.3% reduction in NICU LOS (95% CI, −38.0% to −12.4%; p < 0.001). Shorter engagement durations were associated with smaller reductions, with effect sizes increasing with longer engagement. These findings remained significant in a sensitivity analysis restricted to participants enrolled prior to 28 weeks’ gestation, mitigating time‐dependent bias. Conclusion Longer participation in a clinically integrated virtual maternity program is associated with duration‐correlated reductions in preterm birth and NICU utilization among high‐risk beneficiaries. Virtual models capable of maintaining longitudinal engagement may offer clinical value in managing complex obstetric populations.