Machine-learning and artificial intelligence-driven algorithms guide successfully targeted and tailored educational and motivational reminder text messages in two distinct patient populations: high-risk Medicaid children with asthma, and Medicaid pregnant women at high-risk for preterm delivery. Across both cohorts, 1500 patients have been enrolled over 2 years. Among children with asthma, outpatient visits have increased by 24%; emergency department visits for asthma have decreased by 24%; and asthma controller medication use has increased by 15% (Intervention vs. matched control group). Among pregnant women, prenatal visit attendance has increased by 24% and preterm birth rates have decreased by 27%, with a noticeable trend towards increasing gestational age at delivery (Intervention vs. matched control group). Program satisfaction and retention rates are high. Text messages targeting high-risk patients, and tailored to patients' risk profile, successfully impact health outcomes and improve care experience.