People simultaneously entangled in multiple state systems are often subject to contradictory legal mandates that can foster distrust and incentivize system avoidance. This study focuses on those indebted to both the child support system and the criminal legal system, a situation we describe as dual debt. We ask whether and how the imposition of legal debts with punitive surveillance and collections mechanisms fosters alienation in the form of legal cynicism and estrangement, which we refer to jointly as legal anomie. Drawing from interview data in Minnesota, we find that legal anomie and system avoidance are mutually reinforcing processes, as debts in these systems triggered consequences that pushed people out of the formal labor market and heightened their distrust of legal institutions. The case of dual debt demonstrates how alienating and contradictory policy systems can foster both legal anomie and system avoidance, particularly in the context of economic and social precarity.