This paper describes the development of education of students with special needs in vocational education. The paper is based on a case study research conducted in 2001-2005 in Jyvaskyla Municipal Federation of Vocational Education in Central Finland. The study consisted of two parts: firstly of the historical analysis of special educational stages, and secondly of the contemporary analysis of special educational challenges in the research target. The Developmental Work Research model was used in attempting to get a systemic view of different factors affecting a special educational entity. The study showed the importance of a holistic view. The special educational system in the research target seems to be strongly linked to the general structure of vocational education, its goals, learning principles, legislation and personnel structure. The development of vocational special education in Jyvaskyla followed the strongly regulated national guidelines set for vocational special education until the end of the 1990s. At that time new legislation, structural reforms and the change from norm-based towards an autonomous information-based self-government opened doors for new special educational implementation. From the perspective of teachers specialized in special educational needs (SEN-teachers) a clear change can be seen from an autonomous, defined work towards a loss of an expertise position. However, the strong linkage between general and special education in vocational education offers possibilities for inclusive education. In order to face the new challenges, the work of SEN-teachers has to be redefined to clearly broaden the perspective from teaching towards new expertise in each educational establishment.