Concomitant severe aortic and mitral stenosis in patients who are not candidates for traditional surgery is a complex scenario that becomes increasingly more common with population aging. While transcatheter aortic valve replacement (TAVR) has emerged as a new lifeline for patients with severe aortic stenosis who are at intermediate or high risk for surgical aortic valve replacement, transcatheter mitral valve replacement (TMVR) is still in the early clinical phase. TMVR can be an alternative to surgical valve replacement for high surgical risk patients with bioprosthetic mitral valves, annuloplasty rings, or severe mitral annular calcification (MAC). Despite the growing use of TMVR, left ventricular outflow tract obstruction remains a major challenge and a life-threatening complication of this procedure mostly among patients undergoing valve-in-MAC procedures. Preprocedural planning with imaging is essential in understanding and reducing the risk for these complications.We describe a case of simultaneous transcatheter double valve replacement into native valves from transapical access in a 77-year-old female patient with severe symptomatic aortic and mitral stenosis associated with MAC.