This study aimed to map the evolution of section 24(2) tests and their judicial criticisms. The evolving understanding of the Canadian Charter’s s. 24(2) was developed through three landmark cases: R. v. Collins (1987), R. v. Stillman (1997), and R. v. Grant (2009). The test primarily remained a three-step test since the creation of the Collins test in 1987; however, the focus of the three steps was expanded upon in R. v. Stillman (1997) to include both conscriptive and non-conscriptive evidence and the introduction of two grounds upon which trial fairness can be presumed non-infringed by Charter violations. This framework was almost entirely overhauled and reformed in R. v. Grant (2009), but the three-stage formulation and the consideration of the balance of probabilities remained. However, it most notably placed trial fairness as the overarching systematic goal. Each case presented encompasses the case facts and the resulting s. 24(2) test was concluded by an investigation into their respective judicial criticisms. A discussion of the future of section 24(2) concludes the paper with a look at a newly formulated test steaming from the subsequent jurisprudence.