A 26-year-old woman presents to the emergency department with chest pain, shortness of breath, and cough after traveling to Puerto Rico and exploring caves. She is diagnosed with an acute histoplasmosis infection. Histoplasmosis is a fungal infection endemic to the Mississippi and Ohio River valleys and parts of South America. Common manifestations are flu-like illness with cough, lymphadenitis, and commonly, severe inspiratory chest pain. The elderly and immunocompromised are particularly at risk for severe pneumonia or various extrapulmonary complications. This can be difficult to diagnose and is commonly only discovered after patients fail to respond to multiple courses of antibiotics for “atypical pneumonia.” Fungal pneumonia should be in the differential for patients presenting with these respiratory complaints and careful history-taking can be very helpful in deciding which patients may require further testing.