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Objectives: To invoke behavioral economics theories of ambiguity in the context of offender decision-making, and to test the impact of ambiguity in punishment certainty on offender decisions. Methods: We leverage a quasi-experimental condition among a sample of drunk driving arrestees that are tested for alcohol use and subject to mandatory brief incarceration for a violation. The treatment condition relaxes a zero-tolerance alcohol rule, thereby introducing design-based ambiguity surrounding the certainty of punishment. We use Mahalanobis matching and propensity score weighting methods to estimate the impact of ambiguity on violations. We then interrogate this finding with complementary sensitivity analyses. Results: When facing the ambiguity condition participants are 27–28 percentage points (84–93 percent) more likely to violate program conditions after 30 days of supervision. We demonstrate that a statistical difference in violations due to ambiguity is still detectible at 90 and 180 days of supervision. These results are robust to alternative specifications and falsification tests. Conclusions: This study is the first to examine the impact of ambiguity on criminal justice program compliance using a quasi-experiment from the field. We further demonstrate the unintended costs to persons under supervision and jurisdictions of laxity in program design, which are applicable across criminal justice domains. [ABSTRACT FROM AUTHOR]