Background: Healthcare labor market shortages due to migration, inadequate investments, and lack of continuous training are essential concerns in the Eastern European region. This article aims to describe and reflect on the experience with the implementation of continuous medical education among mother-and-child healthcare providers in Ukraine, including achievements, challenges, and barriers. We analyze this case based on two international collaboration initiatives: the Swiss–Ukrainian program in mother-and-child health that ran from 2000 to 2015, supplemented by the recent Ukrainian–Swiss project “Medical education development” in 2018–2023. Methods: We use a case study approach as the methodology for our study. We collected data from documents (project reports reviews) and in-depth interviews with stakeholders. We apply the method of directed qualitative content analysis. Results: As a result of the Swiss–Ukrainian collaborations, the knowledge and awareness of medical personnel were greatly improved. Modern clinical concepts not well understood at the outset became commonplace and were incorporated into clinical activities. Nevertheless, obstacles to the implementation and rapid uptake of changes were found in the lack of knowledge of the English language among medical doctors, the fear of changes, and the lack of openness and readiness for novel evidence-based clinical practices. However, primary healthcare practitioners in this new project seem to be more inclined to change. Conclusions: A modernized continuous medical education which is based on the values of openness, respect, dialogue, and professionalism can be implemented with the input of an international assistance program despite the resistance of the system towards change.