Despite having endured significant terrorist incidents over the past 50 years, terrorism-specific offenses were not criminalized in Canada until the implementation of the Anti-Terrorism Act (ATA) in 2001. One of the primary goals of this legislation was to provide law enforcement with the tools necessary to proactively prevent terrorist incidents; however, the effectiveness of these new legal measures in preventing terrorist incidents, and the potential for the increased punishment of offenders sanctioned under them, remains unclear. Using a sample of convicted terrorist offenders (n = 153) from the Officially Adjudicated Terrorists in Canada (OATC) dataset, the current study investigates variability in the sentencing outcomes of offenders sanctioned in Canada between 1963 and 2010. The findings indicate that offenders were significantly less likely to successfully complete an offense following the implementation of the ATA; however, offenders previously convicted of general Criminal Code offenses were sanctioned more harshly than those convicted of terrorism-specific offenses alone. Furthermore, changes in the legal processing, and demographic structure, of terrorist offenders are uncovered as the findings highlight how changing contextual environments impact the sentencing outcomes of terrorist offenders.