The complexity of local situations in which agricultural value chains are enacted requires a systemic understanding when seeking to improve interlinked livelihoods. Studying the fresh pineapple value chain in Uganda offers an illustrative example. Individually negotiated and context-specific actor relationships, along with their connected activities can be revealed by conceptualizing the chain as a purposeful human activity system. We followed a systems learning approach to elicit value chain actors’ perspectives on factors influencing their activities while surfacing relevant problem situations, resolutions and constraints. Participatory methods, including cognitive mapping, were used to spark dialogue during meetings with only farmers, traders and brokers and also with mixed groups. The results present the multiple natural, technical and social factors identified by value chain actors leading to losses and benefits to their income. System driving and shaping influences included infrastructure, seasonality, perishability and weather conditions. Process-oriented analysis of multi-stakeholder discussions revealed feedback cycles related to fragmentation of the chain. This resulted from and contributed to problematic communication, price fluctuations and challenges in actor relations. For example, actors proposed uniform pricing and debated the implications. Although the systemic perspective brought forward actors’ awareness of potential benefits of improved collaboration and recognition of interdependent activities, it also exposed barriers. Participatory systems learning helped to capture actors’ room of maneuver, and can support processes towards actor-driven change.