The study investigates how two-sided military exercises affect learning and participating personnel's ability to perform tasks safely when confronted with an equally matched opponent. Data were collected from two separate events the Northern Wind 2019 Final Planning Conference and the Northern Wind 2019 exercise using participatory observations and shadowing. The outline of the critical incident technique was used as a guide when designing the data collection and the activity theory framework was used for coding and analyzing the data. The results indicate that a driven desire to win two-sided military exercises can create unsafe work practices by performing work tasks without regard for occupational-, electrical- or fire safety. The results also indicate a need for reshaping the conception of a two-sided military exercise by treating the exercise as a learning opportunity and recognizing the impact of the participating unit on each other’s learning. The study is based on the results of one army exercise and requires further research to understand the activities that take place and how they affect learning and safety. However, it gives some insight into the learning problems occurring during military field exercises.