This study explores the issue of interpreters’ positionality as outsiders to the forces’ personnel and insiders to the local communities. Twenty local interpreters who worked in the different peacekeeping operations (PKOs) in the Bosnian War, and seven members of the forces’ personnel were surveyed on their personal and professional background, their experiences with working conditions and training as well as the particularities and challenges of PKOs. The results indicate that the status, motivations, hiring procedures, and working conditions of the interpreters changed under the different PKOs, and that this had an impact on the positionality of the interpreter. The findings suggest that specific training programs are needed to better train interpreters to work in PKOs, and that consideration should be given to the issue of how to better train peacekeeping forces to work with interpreters.