This article looks at how welfare conditionality is delivered at the street level. It argues that the street‐level delivery of welfare conditionality is structured by policies, the governance context in which workers deliver welfare conditionality, the organization in which they work, and the occupation they are part of. Characteristics of these contexts present street‐level workers with a variety of signals and incentives that direct their decision making. The article elaborates on this proposition on the basis of a review of academic studies analysing the street‐level delivery of various aspects of welfare conditionality: the use of sanctions, service personalization, and the treatment of vulnerable clients. The review shows that context characteristics together have a significant impact on the street‐level transformation of welfare conditionality policies into practices. Street‐level decision making concerning the use of sanctions is far more complex than can be captured by a perspective on street‐level workers as merely policy implementers. Sanctioning practices are sometimes harsher, sometimes more lenient than policies lead us to expect. The “soft” side of welfare conditionality—represented by service personalization—is often under pressure at the street level, potentially strengthening welfare conditionality's tough side. This affects vulnerable jobseekers most: Street‐level studies show that the balance between disciplining and enabling aspects of welfare‐to‐work is most at risk for more vulnerable groups. The article concludes that the contextual pressures street‐level workers have to deal with in their daily work hardly reflect the “delicate equilibrium” that they need to deliver welfare conditionality in a professional, responsive, and responsible way.