Cuba’s healthcare system is lauded on the Global Health stage as renowned. Low mother/infant mortality rates paired with low infectious disease transmission rates have garnered Cuba’s maternal and primary healthcare systems significant fame. In addition to these healthcare feats, Cuban women experience challenges in finding access to basic forms of over-the-counter care. The Cuba Paradox emerges in which a Cuban woman’s healthcare experience in places such as Mayajigua, Cuba (407 km southeast of Havana) is characterized by access to acute care (expensive treatments such as IVF) and lacks of access to active care (over-the-counter products such as Acetaminophen/Ibuprofen and feminine hygiene). This study aims to investigate the primary and reproductive care paradoxes presented to Cuban women today, specifically in rural Mayajigua, Cuba. A Mixed Methods approach that synthesizes information from a 2015 independent research quantitative survey alongside a 2016 independent research ethnographic project were used to assess the Cuban Medical Paradox in a holistic manner. Analysis showed that the Cuba Paradox exists due to a series of recent international developments, notably the 2016 Cuban Special Period. These results have implications on the study of the Cuban healthcare system at large in addition to implications for healthcare policy assessment beyond Cuba.