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This article analyses the way community-based supervisors build their relationship and interpersonal skills in the context of the system of conditional sentences (house arrest) in Quebec. Based on an analysis of how supervisors decide to allow offenders to spend time outside their home (authorizations), the article aims at understanding how supervisors manage the tensions resulting from the seemingly opposing goals of help and control; and how they integrate the constraints of the system into their decision-making process. The results show that authorizations can be used as a tool for intervention, collaboration or social reintegration. They underline that these practices are intrinsic to a system based on risk management, but also evolve with offender relationships and the trust created between supervisor and offender.