Medical educators have been tasked to provide Cuban-trained Foreign Medical Graduates (FMGs) with adequate learning exposures to become integrated into the South African healthcare workforce. International research suggests that FMGs face multiple challenges during the transition from practising medicine in countries other than where they had been trained. The transitional experiences of international FMGs are well documented, but little is known about the challenges faced by Cuban-trained graduates upon reintegration into South Africa. An improved understanding of the challenges will provide insight into how medical educators can best support Cuban trained graduates in their final phase of training in the South African context.This study explored the challenges experienced during the professional transition of Cuban-trained FMGs with reference to Schlossberg's transitional theory. A qualitative case study was used to interview a purposive sample of 20 Cuban-trained FMGs who studied between January 1997 and December 2007. Data were collected through audio-recorded, semi-structured interviews, which were analysed thematically. The findings indicate that FMGs' experienced educational and social stress, which was linked to the transitional situation itself. Challenges during reintegration included bias and discrimination, language, educational differences, and becoming familiar with patients from diverse educational and cultural backgrounds. They drew on peer and institutional support that was mainly informal and varied across disciplines and the medical schools. Recommendations include a national multidisciplinary consolidated approach to provide personal and professional support at national, institutional, and departmental levels. The creation of mentoring networks will optimise Cuban-trained FMGs' transitional experiences for returning students.