Background: This study examines the health security of both Lebanese citizens and Syrian refugees in Lebanon. It also assesses the readiness and resilience of the healthcare system in response to the multi-layered crisis that began in late 2019. Methods: A qualitative case study design was employed, utilizing 2 unstructured interviews with health experts/hospital staff, semi-structured interviews with 20 Lebanese participants and a document review. Thematic analysis was used to analyze the data. Results: The study found that Syrian refugees have access to health services under terms, conditions and restrictions including out-of-pocket (OOP) payment. In contrast, Lebanese citizens find traditional health guarantor systems largely ineffective, leading to high OOP costs for most healthcare services, with few exceptions. This study reveals a paradox in healthcare access within Lebanon’s fragile environment. Syrian refugees have greater access to health services, with minimal out-of-pocket (OOP) costs to a certain extent, compared to Lebanese citizens themselves who remain entrenched in inadequate health support services and poor public administration. Conclusion: To address this, targeted interventions and policies are crucial for policymakers and stakeholders, including the private and public sectors, local non-governmental organizations (NGOs), and the international community. Reforms are needed, spearheaded by the Ministry of Public Health (MoPH), other relevant ministries, and government payers, to refinance the traditional guarantor system and restore Lebanese citizens’ health security. Additionally, unifying health coverage across all government payers is vital.