A consistent decline in the number of applicants to cardiothoracic and vascular surgery (CTVS) training programs has been observed across the country over the last few years. This disenchantment with the speciality will lead to a shortage of trained CTVS surgeons at a time when incidence of cardiovascular diseases is continuously rising in India. The aim of the study was to reflect on the reasons that averted applicants from pursuing a career in CTVS and measures that would make CTVS a more attractive option to future applicants. An online nationwide prospective cross-sectional survey was conducted. The participants were from a pool of general surgery residents/residents who had just completed the training. A 5-point Likert scale was utilized to rate and evaluate the factors influencing CTVS as the primary choice, factors influencing any super-speciality, and factors that would aid in decision-making and encourage an interest in CTVS. A total of 618 responses were obtained, 25.6% (N = 158) of the responses were from female residents. Only 10.7% (N = 66) of the respondents wanted to pursue CTVS as their primary choice. While interest in CTVS among the 1st year residents was 26%, it was further observed to decline to 18.72% after completion of training. The main disincentives for pursuing CTVS were the need for a hospital with required infrastructure and the dependence on a multi-disciplinary team. The perception of the participants that the cardiologist will take over CTVS procedures was another misguided but important factor. Those residents interested in pursuing CTVS identified the dynamic nature of the speciality as well as the thrills of being a cardiac surgeon as important motivators. Participants felt that adding catheter-based technology to the CTVS curriculum, mandatory CTVS rotation during surgical training, and closer interaction with CTVS residents will generate more interest in CTVS. Although surgical residents report early interest in CTVS, a lack of adequate exposure to the speciality leads to a decline in interest in CTVS. An overhaul of the surgical training that mandates rotating to CTVS, increased interactions with medical students and surgical trainees by CTVS faculty, and incorporation of catheter-based training in the CTVS syllabus is urgently required to increase the number of applicants to CTVS. The online version contains supplementary material available at 10.1007/s12055-022-01406-2.