Although some European countries have initiated systemic transformation towards inclusive education since the ratification of the CRPD, the Austrian school system persists in the segregation of mainstream and special schools and is administered by the allocation of special educational needs (SEN). The SEN assessment attempts to provide individual support to foster pupils' learning by diagnosticing disabilities and deviant behaviour. This circumstance contradicts an understanding of inclusive education without medical and psychological orientated categorisation. The multi-perspective case study contributes to the debate on the requirements of inclusive education and the SEN assessment using the methodological approach of Situational Analysis to understand the experiences of teachers within the inclusion assessment complex. The article follows the research question: How do teachers deal with the dilemma resulting from the requirements of inclusive education and the SEN assessment in Austria? The data set consists of seven focus group discussions with 21 stakeholders (administrators, teachers, and pupils). The findings show that the renewed SEN policy and assessment caused several dilemma. Negotiating this ambiguity is highly dependent on how teachers understand inclusion and to what extend they use their autonomy and discretion to enable inclusion in pedagogical settings.