Infective endocarditis (IE) is a rare and potentially fatal disease. It is an infection of the endocardium of the heart and heart valves. One of the major complications faced by patients who have recovered from a first episode of IE is recurrent IE. Risk factors for recurrent IE include intravenous (IV) drug use, prior episodes of IE, poor dentition, recent dental procedures, male gender, age over 65, prosthetic heart valve endocarditis, chronic dialysis, positive valve culture(s) obtained at the time of surgical intervention, and persistent postoperative fever. We present a case of a 40-year-old male with a history of former IV heroin use who experienced multiple episodes of recurrent IE caused by the same pathogen, Streptococcus mitis. This recurrence occurred despite the patient completing the appropriate course of antibiotic therapy, undergoing valvular replacement, and maintaining drug abstinence for two years. This case highlights the challenges associated with identifying the source of infection and emphasizes the need to develop guidelines for surveillance and prophylaxis against recurrent IE.