The 2022 Monkeypox Outbreak has spread globally in just a few months and has raised great concerns regarding disease recognition due to frequent atypical presentations and questions regarding the possibility of sexual transmission. In endemic countries and prior outbreaks, the clinical manifestations of monkeypox have been well documented, with cutaneous findings following a set, synchronous pattern of evolution. We present two cases of atypical monkeypox presentations in individuals living with HIV, both complicated by herpes simplex virus type 2 (HSV-2) coinfection and elevated troponins, and both demonstrating the ease with which monkeypox can be overlooked in the current outbreak.