In 2005, the province of Manitoba proclaimed the first ever legislation regarding the education of students with special needs, the Appropriate Educational Programming Amendment to the Public Schools Act (Manitoba Education, Citizenship and Youth, 2005). In the accompanying regulations and standards, school principals were legally designated as the educators responsible for ensuring the application of the legislation within their school settings. In this qualitative research study, 15 school principals in northern Manitoba were interviewed regarding their perspectives as to their abilities to comply with their legislative mandates. The findings detail the principals‟ perspectives regarding their knowledge and application of the legislation, their identified supports, and their challenges, including imprecise terminology, contradictory influences, the role of parents, and the provision of specialized assessment. Their beliefs regarding why they must comply, repercussions of non-compliance and recommendations to the Manitoba Government to monitor their compliance are also described. Through the development of a framework, “Enabling Conditions Supporting Principals‟ Compliance with New Special Education Legislation: A Shared Responsibility”, the necessity for principals to collaborate with the provincial government, their school division and their parent community to successfully comply with the new legislation is revealed. The need for sustained effective professional development opportunities, for clarity of terminology, roles and responsibilities and for system accountability by divisions and the province are discussed.