Diagnosis of a neutrophilic dermatosis, such as pyoderma gangrenosum (PG), often is challenging at onset because it can be impossible to distinguish clinically and histopathologically from an acute infection in an immunosuppressed patient, necessitating a detailed patient history as well as correlation pathology with microbial tissue cultures. The dermatologist's ability to distinguish a neutrophilic dermatosis from active infection is of paramount importance, as the decision to treat with surgical debridement, in addition to an antibiotic regimen, can have grave consequences in the misdiagnosed patient. We present a case of PG occurring at a chest tube site in a patient with chronic lymphocytic leukemia (CLL) and highlight the challenges and therapeutic importance of arriving at the correct diagnosis.