Background <p>The COVID-19 pandemic disrupted global medical training and resulted in substantial alterations in the psychosomatic health of medical students. We conducted a comparative evaluation across diverse socio-cultural and economic settings in Kenya (LMIC) and Germany (HIC) to examine the changes wrought to students during the COVID-19 pandemic, their experiences and responses to ease the pandemic burden. We also assessed their attitudes towards the online training model that was introduced during the COVID-19 pandemic with an aim to develop effective educational approaches that could be adopted in learning institutions and offer support in future unpredictable events.</p> Methods <p>We conducted a retrospective cross-sectional web survey three years post the announcement of the first COVID case among undergraduate medical students at the University of Nairobi, Kenya (UoN) and at Charité – Universitätsmedizin Berlin, Germany. Questionnaires were used to assess COVID-19-specific changes in the learning situation, evaluation of mental burden, satisfaction with the online learning (OL), and coping mechanisms of the students. Binomial and multiple regression analyses were applied.</p> Results <p>In total, 122 undergraduate medical students participated in our cross-sectional pilot study (response rate: 78.71%). Respondents were from the UoN (65.5%) and Charité (34.4%). Kenyan and German students experienced similar levels of depression (PHQ-2^COVID) (M = 2.12; SD = 1.36 and M = 2.02; SD = 1.22, <i>P =</i> 0.960) and anxiety (GAD-2^COVID) (M = 2.09; SD = 1.54 and M = 1.91; SD = 1.59, <i>P</i> = 0.540) during the COVID-19 pandemic. For Kenyan students (M = 3.12; SD = 0.60) the transition to OL during the COVID-19 pandemic seemed to be a more comfortable way of learning, compared to the German students (M = 2.91; SD = 0.61). However, the OL score difference was not statistically significant (<i>P</i> = 0.078). In regards to mental health during the pandemic, most students from both countries attributed social support from either family, friends, or religious institutions as a benefactor in coping (UoN: 50.0%, Charité: 59.5%). Most of the students from UoN (40.0%) identified with hobbies such as movies, reading, writing, and social media, while German students (33.3%) identified with sporting activities such as gym, walks and workouts.</p> Conclusion <p>There was significant negative impact on both medical training and the psychosomatic state of medical students in the survey. Such a comparative approach provides insights that isolated single-country studies cannot, thereby contributing to global medical education policy and guiding context-appropriate interventions for future crises.</p>