Since there is little prior knowledge on the effects of case management on offenders behavioral patterns, this paper aims to identify how the activities carried out by probation officers has impacted supervised persons, but also to draw useful conclusions regarding ethical standards in case management. The topic of this paper is of real interest to probation practitioners, as conducting the supervision process, preparing pre- and post-sentence reports in the course of assistance and counseling activities, and the specific nature of interactions with beneficiaries of Probation Services inherently lead to the emergence of ethically challenging situations. The foundation of this topic lies in the need to explore and analyze the nature of these dilemmas, their frequency, the ways counselors respond when faced with ethical ambiguity, identifying optimal responses and reactions from a deontological and ethical perspective, and ultimately outlining best practices. Although this topic is extremely broad, in this paper the focus is on the counselor-beneficiary relationship, being mindful of the numerous aspects that can be addressed, as highlighted in discussions with colleagues from various services and in the final question of the questionnaire used in this study. As a result of the research undertaken, I aimed to present how we, as probation counselors, analyze and manage various dilemmas encountered in daily practice, relevant legislative guidelines, and optimized response strategies. In the end, the conclusions provide an opportunity for reflection and learning, which can offer a greater degree of confidence, security, and control over these situations.