Healthcare and social insurance programs operate at the intersection of economic theory and public policy, confronting challenges such as agency problems, moral hazard, and inefficiencies. This dissertation examines how technology investment shapes healthcare provision, social health insurance plan designs, and the consumption smoothing benefit of disability insurance programs. The first essay investigates how investments in diagnostic coding reporting technology — specifically, the adoption of the International Classification of Diseases, Tenth Revision, Clinical Modification (ICD-10-CM) — impact healthcare provision. Using a difference-in-differences approach, I examine whether more precise diagnostic information reporting influences orthopedic aftercare utilization and costs through indirect financial incentives. The results suggest that mandatory reporting of diagnostic severity leads to an increase in aftercare visits, primarily driven by additional physical therapy sessions. These findings provide new evidence on the role of indirect financial incentives embedded in information reporting within the healthcare system. The second essay examines the privatization of social health insurance programs, focusing on Medicare Advantage (MA). It disentangles the selection threat with pre-65 healthcare utilization by comparing outcomes between MA enrollees and those in Traditional Medicare (TM) to assess the impact of MA on healthcare use, quality, and fiscal costs. The study finds that MA reduces healthcare utilization by 6% relative to fee-for-service (FFS) in the first year of enrollment, with larger effects in subsequent years, without significantly compromising care quality. Additionally, the findings reveal substantial heterogeneity in utilization and cost patterns, driven by favorable selection and the managed care plan designs. The study also uncovers inefficiencies in risk adjustment mechanisms that exacerbate fiscal burdens. This essay contributes to ongoing debates on the role of privatization in government-sponsored health insurance, offering policy insights into improving risk adjustment, the design of managed care plans, and the administration of social health insurance programs. The third essay examines the financial effects of U.S. disability programs by linking Social Security Disability Insurance (SSDI) and Supplemental Security Income (SSI) records with various public and proprietary financial data. Exploiting variations induced by an age-based eligibility rule, the study estimates the impact of disability benefit receipt on bankruptcy, foreclosure, housing transactions, and eviction. The results indicate that disability benefits serve as both a crucial safety net and a mechanism for mitigating broader economic distress. The study findings reflect true reductions in financial distress. Accounting for these extreme events increases the optimal disability benefit amount and suggests a shorter optimal waiting time between application and benefit receipt. Together, these essays advance our understanding of how regulatory reforms, financial incentives, and market structures influence healthcare delivery and social insurance. The findings have important policy implications for optimizing healthcare technology adoption, improving the efficiency and equity of social insurance programs, and designing more effective safety nets for economically vulnerable populations.