We present the case of a 42-year-old man with mitral valve prolapse (MVP) and infective endocarditis. He was referred to our hospital by his family physician for the evaluation of a cardiac murmur. A detailed medical history revealed that he had been feeling fatigue with occasional episodes of slight fever during the last two months. Echocardiography revealed MVP with a sizeable vegetation and severe mitral insufficiency. Serial blood cultures were positive for Streptococcus viridans, highly penicillin susceptible. He was put on appropriate antimicrobial therapy, but both the vegetation and the concomitant mitral insufficiency persisted after otherwise successful medical therapy. Thus, the patient underwent surgical vegetectomy with mitral valve repair. He had an uneventful postoperative course and remains free of disease at the 12-month follow up. Our case report reinforces the value of early diagnosis in the presence of a high clinical suspicion of MVP endocarditis. An extended clinical workup, including serial detailed echocardiography studies, is mandatory in such a patient. Medical treatment of infective endocarditis in the setting of MVP is often successful. However, cardiac surgical intervention plays an important role in the treatment of intracardiac complications. Mitral valve repair in the context of a healed and stable infective endocarditis is the treatment of choice.