Typhoid, otherwise known as enteric fever, and measles both have a high incidence worldwide. However, a coincidence of both has been only documented twice previously in 1866 and 1949. We present a case of a 24-year-old male who presented with high-grade fever and diffuse abdominal tenderness. He was diagnosed with typhoid initially, but during the course of his illness, he developed a maculopapular rash and pathognomonic Koplik’s spots. Further investigations confirmed measles that was concurrent with typhoid. This highlights the importance of further comprehensive investigations even in diagnosed cases, and that overlapping symptoms should raise the clinical suspicion of concurrent diseases. One should always keep an open mind when assessing a patient, not just at the time of making a diagnosis but throughout the course of illness.