Although health insurance is a critical tool for wellbeing across the life course, few studies have explored the long-term health implications of shifts in insurance coverage. This study examined whether changes in insurance types from adolescence to early midlife were associated with early midlife self-rated health. This study used data from Wave I (1994-1995; average age 15.7 years), Wave IV (2008-2009; average age 28.7 years), and Wave V (2016-2018; average age 37.6 years) of Add Health, including 6,765 respondents from 1994-2018. Logistic regression was used to examine the association between health insurance status from adolescence to early midlife and early midlife self-rated health. The analyses were conducted from March - August 2024. Relative to having private insurance in adolescence and early midlife, the following health insurance statuses in adolescence and early midlife were significantly associated with poorer early midlife self-rated health: public in adolescence and early midlife (AOR=3.34; 95% CI=1.89, 5.91); uninsured in adolescence to public at early midlife (AOR=3.29; 95% CI=1.85, 5.85); private in adolescence to public at early midlife (AOR=3.36; 95% CI=2.46, 4.58), and private in adolescence to uninsured at early midlife (AOR=1.68; 95% CI=1.10, 2.55). Health insurance statuses from adolescence to early midlife, specifically having or switching into public insurance, may be associated with poorer health in early midlife among individuals who were adolescents in the early 1990s. More research is needed to explore how insurance reform such as the Children's Health Insurance Program may have mitigated this association in future cohorts.