Many bacterial, viral, and fungal co-infections have been reported with COVID-19-associated acute respiratory distress syndrome (ARDS). Invasive Aspergillosis has been described with COVID-19 ARDS. However, it continues to evade diagnosis in critically ill patients admitted to the intensive care unit (ICU). The difficulty is discerning an actual infection from colonization. Unfortunately, a timely diagnosis is crucial since COVID-19-associated pulmonary Aspergillus (CAPA) has high morbidity and mortality. We present three ICU cases of CAPA to illustrate the difficulty in diagnosing and treating the disease. We hope to bring awareness and improve patient outcomes of CAPA.