This dissertation examines how actors within Canada's penal voluntary sector identify, navigate, resist, and strive to eliminate structural stigma and collateral consequences of punishment. Using an approach to qualitative research informed by institutional ethnography, anti-oppressive practice, and public criminology, my research explores how practitioners attempt to support people with criminal records despite many exclusionary policies and practices - including those enforced by the penal voluntary sector itself - that create obstacles to various social domains (e.g., employment and housing). This research is motivated by my experience working in the penal voluntary sector during a period (2006-2015) in which many punitive policies, including changes to Canada's Criminal Records Act, were brought into effect by a federal Conservative government and maintained by a subsequent Liberal government. To understand the penal voluntary sector's role in supporting people with criminal records in the community, I conducted twenty-two interviews with various sector actors. I also attended several conferences, meetings, and events alongside practitioners to stay connected to the sector and ensure an ongoing understanding of the important issues to people with criminal records and those who support them. Additionally, I incorporated analysis of texts (e.g., policies, forms/assessments, public consultation reports, parliamentary committee studies) to frame the political, institutional, and social relations that shape the day-to-day experiences of practitioners and the people they support in the community. Finally, I engaged public criminology as part of my research methodology and included reflections on my advocacy work throughout the dissertation. While critical sociologists and criminologists mostly describe the penal voluntary sector as a net-widening mechanism, I maintain that understanding the day-to-day work within the sector is crucial to identifying, navigating, resisting, and eventually eliminating structural stigma and collateral consequences of punishment. Additionally, I contend that spaces where practitioners meet (e.g., conferences) are key sites for developing communities of care through which academics, practitioners, advocates, and people with criminal records can work towards a just transition from penal and other related systems (e.g., homelessness). Finally, I reflect on academia's role in resisting and eliminating carceral power and structural stigma and on the lessons learned from my efforts at doing so.