Paravalvular leak (PVL) after mitral valve replacement is the most common type of nonstructural prosthetic valve dysfunction. While most patients with only mild-moderate PVL are asymptomatic, those with severe PVL can present with heart failure and hemolysis, leading to significant morbidity and mortality. Surgical correction has remained the gold standard therapy for symptomatic PVL; however, for high surgical risk patients, percutaneous approaches have emerged as an alternative management. With the emergence of transcatheter mitral valve-in-valve techniques for failed bioprosthesis and rings, valve-in-valve PVL is being encountered more frequently and is identified as a challenging entity. We present a case of a symptomatic patient with a moderate – severe valve-in-valve PVL after two mitral valve replacements who then underwent a transcatheter mitral valve-in-valve-in-valve implantation with a 29mm Edwards® SAPIEN3 valve via transseptal approach. This unique case highlights the complexity of this clinical entity and recognizes three-dimensional transesophageal echocardiography as a tool to guide valve-in-valve PVL closures.