Transcatheter aortic valve implantation (TAVI) is the default therapy for most elderly patients with severe aortic stenosis, but outcomes in complex anatomy depend on imaging-guided planning and disciplined technique. This article aims to present our institutional approach, supported by the current literature, in managing several challenging anatomical scenarios. We focus on seven high-impact scenarios—bicuspid aortic valve (BAV), hostile transfemoral access, iliofemoral/aortic tortuosity, adverse aortic angulation, heavy annulus/Left Ventricular Outflow Tract (LVOT) calcification, small annulus, and risk of coronary obstruction—and propose a practical approach to minimize the risk of complications. In BAV, current generation transcatheter heart valves (THV) achieve favorable early outcomes when sizing accounts for supra-annular constraints and implantation depth is tailored. Transfemoral access remains dominant in contemporary registries, yet a meaningful minority of cases require adjunctive peripheral vascular intervention to enable THV delivery-system passage. In case of annulus or LVOT calcification, small annuli, complex aortic anatomy, high risk for coronary obstruction, and pre-procedural Computed Tomography (CT) allow for an accurate sizing of THV and tailored procedural planning. A structured, CT-driven pathway that links anatomic findings to specific facilitation and bailout steps can standardize decision-making and improve safety across these challenging scenarios. We strongly highlight the importance to build a network where most complex procedures are carried out in Valve Centers where expert operators are trained to manage high volume, high complexity, and difficult complications.