Systems development of wind turbine control is competitive with respect to innovation, time and cost. So how can learning possibly occur under such circumstances? Dewey’s pragmatist approach to learning is adopted, emphasising reciprocity between the systems developer’s individual experience and the sociotechnical practice. The framework involves the concepts of sociotechnical practice, anchoring of indeterminate situation, and strip of doings towards determinate situation. An ethnographic study was made of four cases of systems development and learning do occur in the cases, enabled by converging anchoring of the indeterminate situation and the systems developers' different experience. However, an extreme case reveals initiated learning processes and that the interchanges between materiality of the artefacts and systems developers block the learning processes due to a customer with imprecise demands and unclear system specifications. The specific contribution of the paper is the understanding of the individual systems developer’s learning, complemented with the possibility for collective learning and the mechanisms of blocked or derailed learning processes. The practical implications are that managers of systems development should ensure that constitutive means are present, and specifications are sufficiently obdurate. Too ductile means, such as customers with unclear demands, can block or derail learning processes.