Aortic root replacement (ARR) introduces several anatomic complexities relevant to valve-in-valve (VIV)-transcatheter aortic valve replacement (TAVR) that may (1) increase the risk of coronary obstruction, (2) necessitate transcatheter valve overexpansion to accommodate large annuli, and (3) require alternative vascular access to navigate aortic kinking. Therefore, we aimed to quantify the feasibility of VIV-TAVR in patients who underwent aortic root surgery. Postoperative computed tomography scans were reviewed for consecutive patients who underwent ARR between 2005 and 2019 to obtain measurements relevant for VIV-TAVR planning. Virtual transcatheter valve to coronary ostia distance was measured to assess the risk of coronary obstruction. Root morphologies were classified into 1 of 4 groups based on aortic graft type, aortic diameter at the sinotubular junction, sinus height, estimated transcatheter heart valve height, and diameter. VIV-TAVR was projected to be complex in patients with an aortic kink, extremely large annulus, or heightened risk of coronary obstruction. Among 848 patients who underwent ARR during the 15-year study period, qualifying contrast-enhanced scans post-ARR were performed in 81 patients. Complex VIV-TAVR was anticipated in 50.6% of subjects. Patients with abnormal root anatomy experienced increased odds of complex VIV-TAVR relative to patients with normal root physiology (ie, sinotubular junction diameter>transcatheter heart valve diameter, sinus height>transcatheter heart valve height) or those who received straight tube grafts (odds ratio, 4.53 [95% CI, 1.02-20.1], P=0.046). The odds of complex VIV-TAVR were also higher among patients who underwent aortic valve replacement-ARR with a stentless bioprosthesis (stentless versus stented, odds ratio, 4.63 [95% CI, 1.40-15.3], P=0.012; stentless versus valve-sparing ARR, odds ratio, 3.78 [95% CI, 1.14-12.5], P=0.029). ARR patients with atypical root morphologies or those who underwent valve replacement with stentless bioprostheses may be at high risk for complex VIV-TAVR. Prospective evaluation is required to assess the impact of these conclusions on procedural feasibility.