The rhetoric and philosophy of community supervision is moving toward rehabilitation, spurred in part by the emergence of evidence-based practices. However, there remains a great deal of tension between punitive and rehabilitative approaches in supervision. This chapter offers a brief history of this tension, with consideration of how macro-level sociopolitical forces affect micro-level practitioner efforts to balance their dual roles as helper and enforcer. Following this, we focus on the ways the tension appears in the present-day context by providing an empirical review of both the punitive sanctions and rehabilitative techniques routinely used in supervision. Our review of rehabilitative techniques includes the dominant risk-need-responsivity (RNR) framework and some of its embedded tools: cognitive-behavioral therapy (CBT), working alliance (WA), and motivational interviewing (MI). We discuss emergent strength-based approaches (SBAs) which shift the focus from an individual's potential risks to their extant strengths. Based on the evidence supporting the RNR, an integrated RNR and SBAs approach will provide a holistic approach to supervision and offer opportunities to provide effective treatment services.