Health insurance plays a significant role in accessing healthcare and financial protection, but working women remain predominantly underinsured even with increased education. The present study examines the relationship between education, poverty, employer sponsorship, and health insurance coverage among working women in Kerala. From a cross-sectional survey of 392 respondents, the study uses Chi-square and regression analysis to quantify the influence of education on insurance awareness and take-up and identify the main constraints such as affordability and employer policies. The study establishes that education boosts awareness but doesn’t necessarily contribute to increased enrollments as money issues and lack of employer-covered benefits remain leading inhibitors. Insured women had better post-pandemic well-being, reduced financial distress, and increased access to care, lending themselves to multi-level interventions. Research recommends employer-provided insurance coverage, economic literacy programs, and subsidized health coverage policies to support women’s economic resilience and security in healthcare.