This article offers a street‐level perspective on welfare conditionality as it was practiced in contracted‐out UK activation programs between 2008 and 2015. Drawing on observation and in‐depth interviews, the article illustrates the ways that behavioral conditionality provided street‐level workers with the means to intensify or moderate activation for particular claimants. Responding to arguments about the curtailment of street‐level discretion, the article argues that in the particular context of target‐driven, work‐first, and otherwise highly constrained services, discretion resided in the ability to intensify or moderate conditionality and its coercive potential—in decisions about how, on whom, and to what extent it would be applied. The article argues that attending to this form of discretion provides an alternative frame through which to view the differentiated treatment typically understood as “creaming” and “parking.” In so doing, the article problematizes accounts that draw clear lines between calculative, normative, and dispositional forms of street‐level reason and practice. It shows how advisors' responses to the “street‐level calculus of choice” were articulated in terms of expectation, where attempts at future‐oriented calculation necessarily entailed making other forms of speculative and normative judgement about claimants and their situations. The article thus contributes to an understanding of both the causes and meaning of differentiated treatment in conditional welfare services.