The definition for special education needs (SEN) and the policies for its assessment varies widely between countries. This paper aims to investigate similarities and differences through a Swedish-German comparative approach. Based on the distinction between categorical and relational perspectives as expressions of specific thought styles, 58 SEN assessment reports from both countries were qualitatively analysed. The results demonstrate the maintenance of the categorical perspective in terms of focusing on the pupil’s ‘failure’. This result is even more notable in the German examples than the Swedish cases. Exceptionally and in both countries, a relational perspective emerges, taking teaching and the social environment into account. In conclusion, we suggest a flexible SEN approach with a stronger emphasis on the relation between the individual and the learning environment.