Far from following a linear process from its conception to its implementation, an educational design often involves discrepancies between what its promoters intended and what the participants actually do. In this paper, drawing from a sociocultural perspective to learning, we focus our attention precisely on some of the discrepancies observed during the implementation of a training program. We consider these discrepancies not as mistakes or misunderstandings, but rather as indicators of the communicative dimension of any intervention and as “windows” on the processes of change and on learning. The program we have studied here was set up in Madagascar and was sustained by a Swiss cooperation agency addressed to farmers in the field of forestry. In this research, we adopted an actor-oriented perspective in order to understand the promoters' and the beneficiaries' interpretation of the design and the way they developed innovative strategies to resolve the difficulties they faced. We chose some “critical incidents” from the data gathered through ethnographical research and show how the whole process of the conception and the implementation of the program was deeply affected by both the power dynamic embedded in the history of the relationship between the Swiss and the Malagasy groups and by their own cultural and institutional constraints. In conclusion, we discuss the significance of an actor-oriented perspective that contributes to a better understanding of the social and cultural dimensions of learning and allows us to relate the here and now micro-phenomena to the larger anthropological, social, and political scenery.