Intentional misunderstandings take advantage of the ambiguity of language to do what someone said, instead of what they actually wanted. These purposeful misconstruals or loopholes are a familiar facet of fable, law, and everyday life. Engaging with loopholes requires a nuanced understanding of goals (your own and those of others), ambiguity, and social alignment. As such, loopholes provide a unique window into the normal operations of cooperation and communication. Despite their pervasiveness and utility in social interaction, research on loophole behavior is scarce. Here, we combine a theoretical analysis with empir- ical data to give a framework of loophole behavior. We first establish that loopholes are widespread, and exploited most often in equal or subordinate relationships (Study 1). We show that people reliably distinguish loophole behavior from both compliance and non-compliance (Study 2), and that people predict that others are most likely to exploit loopholes when their goals are in conflict with their social partner’s and there is a cost for non-compliance. We discuss these findings in light of other computational frameworks for communication and joint- planning, offer a proposal for how loophole behavior might develop, and discuss the implications of this work for human-machine alignment.