Prosthetic valves are being widely used in the treatment of heart valve disease. Prosthetic valve endocarditis (PVE) is one of the most catastrophic complications seen in these patients. In particular, prosthetic valve dehiscence can lead to acute decompensation, pulmonary edema, and cardiogenic shock. Here, we discuss the medical management of late PVE in a patient with a prior history of late and redo early PVE and recurrent dehiscence. According to the present case, we can summarize the learning points as follows. A prior history of infective endocarditis increases the risk of relapse or recurrence, and these patients should be evaluated very cautiously to prevent late complications. Adequate debridement of infected material is of paramount importance to prevent relapse. A history of dehiscence is associated with increased risk of relapse and recurrent dehiscence.