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Despite the growing public debate on bail in Canada, we know little about how individuals accused of crimes experience bail firsthand. While literature exists on incarceration and post-sentencing release, the intricacies of being on bail have received comparatively less attention. This study examines this situation through 30 in-depth interviews conducted with individuals on bail in Ontario, Canada. The focus is on how court-imposed conditions and supervision shape the lives of those on bail. Results suggest that how individuals experience bail is highly subjective, often shaped by one’s social context and background. Many conditions enforced by the courts, such as requiring a surety and abstaining from substance use, make release more onerous for those who are marginalized by factors related to social class, addictions, and housing instability. In setting bail conditions, the courts often fail to recognize the lived realities of many accused, which can perpetuate the cycle of further criminalization. Rather than an alternative to remand custody, participants often saw bail supervision and conditions as restrictive and, in some cases, coercive. The data suggests that while bail is designed and legitimated as a step towards freedom, for some, the realities of such measures make such liberty illusory.