This chapter delves into the challenges and discussion around identifying and supporting disabilities in Aboriginal youth. Despite the global paradigm of inclusion, educators and service providers continue to struggle to understand children's developmental needs so as to inform programs. This process is increasingly complicated by cultural and linguistic differences, in an increasingly diverse student population. Like many regions of the world, Canada has a shifting demographic base and there is growing concern for the cultural appropriateness of traditional approaches to assessment and special education practices. Canada is not alone in struggling to meet the educational needs of its indigenous people and proven practice from one country can help inform the international community. This chapter presents three factors driving this debate in Canada: growing sensitivity to multi-cultural/multi-linguistic differences in our schools; the impact of inclusive education; and recognised criticisms of traditional psycho-educational assessment practices. While the author recognises a place in education for standardised assessment, an argument is presented that current practice, which strives to fit children into funded support categories, has resulted in an overreliance on test scores and a devaluing of teacher and parent perspectives. Certainly, there is growing recognition that such approaches have failed to empower teachers to adapt programs and create effective instruction. Instead the author argues to keep "testing" separate from "teaching" and presents existing culturally sensitive models in Canada which are succeeding in this practice. As such, emerging practice for Canada's Aboriginal population offers food for thought in other regions of the world that are struggling with similar issues. The chapter concludes with a discussion of the implications of this discussion and these models on educational leadership.