This chapter examines the interpretive exercise under the Canadian GAAR, contrasting this interpretive exercise with ordinary interpretation under the textual, contextual and purposive (TCP) approach, and considering the way in which the object, spirit, and purpose of the relevant provisions is determined in order to decide whether an avoidance transaction is subject to the GAAR. The first part distinguishes the interpretive exercise under the GAAR from the TCP approach, explaining that ordinary interpretation under the TCP approach is rightly constrained by the text of the applicable provisions in a way that the interpretive exercise under the GAAR is not. The second part addresses the way in which the object, spirit, and purpose of the relevant provisions is interpreted, criticizing the “unified textual, contextual and purposive” approach adopted by the Supreme Court of Canada in Canada Trustco Mortgage Co.v. Canada, and arguing that separate inquiries into a misuse of specific provisions and an abuse having regard to provisions read as a whole is not only consistent with the Court’s admonition in Canada Trustco against judicial reliance on overarching or overriding policies that are not anchored in the interpretation of the relevant provisions, but mandated by the text of subsection 245(4)