Biliary obstruction is a serious condition with various underlying causes, including malignancy, infection, and gallstones. Fungal biliary infections are rare, frequently misdiagnosed, and carry significant morbidity and mortality. Here, we present the case of an 82-year-old male with multiple comorbidities who developed sepsis secondary to cholangitis. Despite initial diagnostic challenges and the complexity of his biliary anatomy due to prior surgeries, a multidisciplinary approach identified biliary candidiasis as the underlying cause of cholangitis and sepsis. This case underscores the importance of considering fungal infections in the differential diagnosis of biliary obstruction, particularly in high-risk and immunosuppressed patients. Early recognition is essential to enable prompt treatment and improve patient outcomes.