In natural language understanding, a crucial goal is correctly interpreting open-textured phrases. In practice, disagreements over the meanings of open-textured phrases are often resolved through the generation and evaluation of interpretive arguments , arguments designed to support or attack a specific interpretation of an expression within a document. In this paper, we discuss some of our work towards the goal of automatically generating and evaluating interpretive arguments. We have curated a set of rules from the code of ethics of various professional organizations and a set of associated scenarios that are ambiguous with respect to some open-textured phrase within the rule. We collected and evaluated arguments from both human annotators and state-of-the-art generative language models in order to determine the relative quality and persuasiveness of both sets of arguments. Finally, we performed a Turing test-inspired study in order to assess whether human annotators can tell the difference between human arguments and machine-generated arguments. The results show that machine-generated arguments, when prompted a certain way, can be consistently rated as more convincing than human-generated arguments, and to the untrained eye, the machine-generated arguments can convincingly sound human-like.