The United Nations and WHO have summoned governments from low-income and middle-income countries to institute universal health coverage and thereby improve their population’s healthcare access and outcomes. Until now, few countries responded favourably to this international plea. The HIV/AIDS epidemic, a major global public health challenge, resulted in over 11 million orphans in sub-Saharan Africa. Extended families have taken responsibility for more than 90% of these children. HIV orphans are likely to be poorer and less healthy. Burkitt lymphoma is the most common childhood cancer in sub-Saharan Africa. If orphans need lifesaving chemotherapy, appointing legal guardians becomes necessary to access health insurance. However, rules and regulations involved may be unclear and costly. This hinders its access for poor families who need it most. Uninsured children risk hospital detention over unpaid medical bills and have lower survival. Our case report depicts the quest for health insurance coverage of two HIV orphans with Burkitt lymphoma in Kenya.