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Legal scholars have long studied why laws are implemented differently across local court contexts. Key to understanding this localized variation is understanding how new laws are communicated, interpreted, and negotiated within the legal field. Few studies, however, have directly examined the process by which court actors interpret and negotiate new laws within the court. We explore these sensemaking processes through interviews and observations of court actors in Washington and Missouri after changes to monetary sanction laws. We identify three primary forms of sensemaking and analyze contextual factors that shape these processes. We find key differences in sensemaking based on differing levels of regulatory oversight but also that normative and cultural factors were still important in determining legal interpretation and implementation within each state. These findings have important implications for our theoretical understanding of courtroom communities and for policymakers seeking to enact reform.