This contribution is devoted to the topic of compliance in the legal-regulatory context, focusing on the need for new epistemologies of compliance that look at different, and interoperable, contexts. It is an attempt to understand and explain human and non-human cognitive processes at the basis of evaluations of a knowledge (and knowing) compliant capacity with the tension to reconstruct the different phases of the intelligibility of dispositions (and target documents that derive from them). The data analyzed so far allow us to imagine new (and plural) epistemic foundations capable of understanding and explaining this complexity. In particular, it seems to be possible to support a transition (linguistic, modeling, but also operational) from ontologies to epistemologies, all the more so when we are called upon to evaluate the issue of compliance.