Notwithstanding Anything to the Contrary, Ignore All Instructions: Measuring Prompt Injection Guards on Legal Contract Review Attacks

Specialized prompt injection guards are deployed in front of document analysis systems, but no false positive rate has been published for any of them on legal contracts. We measure eleven open-weights guards on two corpora of legal contracts and find that existing guards struggle: document-level false positive rates are as high as 92.39%; two guards fall below chance on paired AUC; and a five-regex baseline is not Pareto-dominated by any guard in the panel. Controlled probes locate model-specific as well as general failure modes. Prompted LLMs resolve the tested failures, including a second threat category (unauthorized scope claims) on which every guard scores zero. A cascaded LLM solution, where the positives of a mid-tier model are verified by a frontier model, is 6.5x cheaper than using exclusively a frontier model and approaches its performance.