There is increasing attention being given to how to regulate AI systems. As governing bodies grapple with what values to encapsulate into regulation, we consider the technical half of the question: To what extent can AI experts vet an AI system for adherence to regulatory requirements? We investigate this question through two public sector procurement checklists, identifying what we can do now, what we should be able to do with technical innovation in AI, and what requirements necessitate a more interdisciplinary approach.