The objectives of this study, which used a quantitative non-experimental design, were to investigate teaching motivations and career perceptions as well as motivational problems of Cuban trainee teachers across two universities in Havana and Camagüey. Participants (N = 340) completed the Factors Influencing Teaching (FIT)-Choice scale which was extended and culturally adapted to the Cuban context. The study used a non-probability convenience sampling method in which participants were chosen based on their availability in lectures. The main motivations for choosing teaching as a career were: (i) making a contribution to society; (ii) shaping the future of children/adolescents; and (iii) prior teaching and learning experiences. Moreover, Cuban trainee teachers generally perceived teaching as a career that is high in demand and low in return in terms of salary and social status. Some motivational problems were also identified: for example, foreign language education students were found to be less intrinsically motivated, and indicated less intention to remain in the teaching profession. Based on the results, suggestions for recruiting and maintaining qualified trainee teachers are provided to overcome teacher shortage in Cuba.