NATO is keen to improve technical interoperability between participating nations. However, according to certain scholars, technical interoperability has been overestimated within the field and other important factors related to organisational interoperability are neglected. The aim of this study is to examine the transformation of Sweden’s organisational interoperability within NATO the last decades. This will demonstrate how Sweden’s organisational interoperability has changed through a period of increased technical complications within military alliances. This dual case study compares Sweden’s contribution in Kosovo and Afghanistan by applying theorganisational interoperability agility model (OIAM). The Swedish Armed Forces have augmented their preparations prior to collaborations which improve their skill to adapt to certain nations. They have also improved their ability to adapt to other leadership styles and structures. However, issues associated with system compatibility have increased and seem to affect military leadership coordination. Sweden’s ability to adapt to other nations cultural differences are restricted between both cases. Technical differences seem to affect military leadership more than combat units whereas cultural differences have a greater impact on soldiers compared with officers.