COVID-19-associated pulmonary aspergillosis (CAPA) is a recently recognized entity associated with the COVID-19 pandemic and known post-viral pneumonia complications. More data are awaited and there has been a recent consensus criteria published hoping to generate more research and registries to inform clinical decision-making. Nevertheless, it is clear that CAPA imposes a worsening disease course of COVID-19 pneumonia with added morbidity and mortality. We present two cases with differing outcomes managed within the limitations of our institute and make reference to the recent consensus criteria. We hope to highlight the importance of considering empirical treatment in the correct clinical context while awaiting the results of microbiological workup as ascertaining the diagnosis of proven CAPA is challenging in the real-world setting.