Monkeypox is an emerging zoonosis that has been declared a public health threat due to its spread outside of endemic areas. We present two cases of monkeypox: one involving a 39-year-old male patient living with HIV on antiretroviral therapy with detectable viraemia and a low CD4 count, and another involving a 44-year-old male, negative for HIV, who visited our Diagnostic and Consultative Unit with a new-onset skin rash. Both individuals identify as men who have sex with men and had travelled abroad before the disease onset. One patient was hospitalised, while the other was treated as an outpatient with follow-up care. Both cases were managed conservatively due to the unavailability of tecovirimat in Bulgaria. We emphasise the importance of recognising and diagnosing monkeypox and the significance of HIV screening, as monkeypox could be considered an AIDS-defining condition in people living with HIV. Maintaining a high level of suspicion for new cases is essential, as instances of monkeypox continue to be reported in non-endemic countries.