This article engages Michel Foucault’s thesis that post-sovereign law would be increasingly colonized by the disciplinary norm. It explores, through an analysis of prisoner litigation surrounding Maryland’s Patuxent Institution and its defective delinquency statute, how disciplinary power is enabled, understood, and resisted through law. I argue that Article 31B (as the defective delinquency statute was known) set up a zone of expert prerogative and discretion actively maintained and legitimated through jurisprudence. Yet, paradoxically, law also functioned as a conduit for resistance and contestation pitting the epistemological premises of discipline against the functions of legal jurisprudence and the foundations of criminal law. I contend that this dual character of law’s engagement with discipline (i.e., at once open to expert “colonization” and site of structural incompatibility and resistance) illustrates the intractability of the relationship between the disciplinary and law. That is, law both constitutes disciplinary space (and within this normative envelope, discipline can be “unbound”) and remains in a state of tension with the forms of power that develop within it (which by their very premises seek to exceed the limits law would place upon them).