Social interest in art integration for curriculum enrichment and innovation, particularly at the turn of the century, has promoted extensive institutional partnerships between cultural organisations and public schools in many countries. Stimulated by social demands for innovative educational practices, these institutional partnerships have increased the numbers of teaching artists sent to schools. These artists are expected to contribute to the development of students' creative imaginations by providing learning opportunities beyond conventional classroom practices. However, the extent to which teaching artists are able to develop creatively within their socially expected roles remains unclear, especially considering the marginal status of the arts in formal education settings. A recent survey- and interview-based study conducted by the present author in South Korea demonstrated that teaching artists in schools find the structured educational system often limits the scope of their classroom practice. This article reviews the teaching artists' concerns and needs identified in the study context and discusses ways to support their professional development and expand the roles of institutions in improving the quality of their teaching practice. The discussion also examines historical and socio-political factors that have influenced the persisting challenges of structural issues inherited in the Teaching Artists in Schools Program in South Korea to provide suggestions for more sustainable and instructive collaborations.