Given the over-representation of Indigenous peoples in the criminal justice system, steps have been taken to enhance the cultural relevance of sentencing, assessment and treatment. Specifically, changes to legislation and sentencing (e.g., s. 718.2 [e] of the Criminal Code, introduction of conditional sentence orders), as well as operational changes (e.g., creation of culturally-relevant programming), were introduced to address over-representation. More recently, the question of whether commonly-used risk assessments contain cultural-bias when applied to Indigenous peoples has been argued before the Supreme Court (i.e., Ewert v. Canada, 2018). To better understand the potential impacts of these legislative and operational changes, and seek to better understand the potentially unique causes of criminal behaviour for Indigenous peoples, three studies were conducted. Study 1 examined the application of conditional sentence orders (CSOs) with a sample of Indigenous offenders (n = 749) compared to Caucasian offenders (n = 1,625). It was found that Indigenous individuals received shorter CSOs and had a higher likelihood of being convicted of breach. However, no differences regarding the number and type of optional supervision conditions were found between groups, after controlling for individual-level factors (e.g., risk level, severity of offence). Study 2 identified and examined culturally-relevant risk/need factors with an Indigenous Advisory Group (N = 51). The process of co-development and thematic analysis resulted in the Culturally-Relevant Factors Questionnaire, consisting of 12 themes (e.g. residential school experience, stability of upbringing, experience of discrimination, extreme poverty). The questionnaire was administered to a sample (N = 36) of Indigenous males on community supervision. Lastly, Study 3 consisted of a meta-analysis examining the effectiveness of culturally-relevant correctional programming with Indigenous offenders. Results based on seven studies (N = 1,731) indicated that Indigenous offenders who participate in these programs have significantly lower odds of recidivism (odds ratio = 0.72) compared to Indigenous offenders who participate in generic programs. The implications of the three studies lend support to increasing the cultural relevance of sentencing, assessment, and programming. Furthermore, they highlight the need to better understand potentially unique or salient factors that can enhance the effectiveness of strategies for Indigenous peoples in the criminal justice system.