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This paper explores the experiences of visitors seeking entry to Canadian penal facilities, focusing on the sociological and criminological implications of prison staff's regulation of contraband and visitor attire. Drawing on our collective encounters as volunteers, researchers, and educators within prisons, we critically examine the policies and practices surrounding prison visitation, with particular attention to the use of intrusive technologies and the policing of clothing. We argue that the imperative to regulate contraband—often framed as a matter of public safety—serves to legitimize harmful practices that alienate and degrade visitors. Additionally, we explore the arbitrary enforcement of dress codes, which disproportionately affect women and reinforce power imbalances within the prison system. These dress codes, ostensibly implemented to control contraband, grant considerable discretionary power to correctional staff, whose interpretations often create uncertainty and vulnerability for visitors. Through personal narratives and critical analysis, we offer insights into the broader challenges faced by those interacting with prisons, emphasizing the need to reconsider visitation practices in a way that upholds dignity, transparency, and the potential for positive connections between incarcerated individuals and their visitors. This paper contributes to ongoing discussions on the tensions between security measures and human rights within prison systems.