Transcatheter aortic valve replacement (TAVR) has increasingly become a fundamental approach for treating aortic valve stenosis (AVS), especially in high surgical risk patients. This case study underscores the criticality of meticulous procedural planning and precise valve selection in patients with severe AVS compounded by obesity. We report a case of a patient who, after receiving a 26 mm Edwards Sapiens 3 valve, presented with worsening exertional dyspnea and a declining indexed effective orifice area (EOAi). This deterioration indicated early structural valve deterioration (SVD), presumably due to patient-prosthesis mismatch (PPM). A subsequent valve-in-valve (ViV) TAVR using a 29 mm Medtronic Evolut Fx valve was successfully executed, leading to a notable improvement in EOAi. This case study emphasizes the complexities inherent in valve choice and sizing in TAVR, particularly highlighting the impact of PPM on obese patients and its potential to precipitate early SVD. The report further explores the emerging strategies in addressing TAVR valve dysfunctions via ViV interventions, shedding light on the nuanced and dynamic nature of TAVR management in obese patients. It advocates for tailored treatment strategies in managing such intricate cases, demonstrating the evolving landscape of TAVR procedures.