This paper explores the experience of 14 teacher-trainers involved in a train-the-trainer digital education program in Switzerland. Data collected between August 2019 and June 2021 through focus groups and collaborative portfolios were analyzed through thematic analysis. A qualitative analysis was used to identify the main factors facilitating or hindering their experiences. These facilitators and obstacles were related to individual characteristics, interactions with stakeholders, instructional content, and logistics. Based on these findings, recommendations are provided to help training designers to maximize the success of such initiatives.