Although lawyers are often engaged to help organizations interpret regulatory directives, we know little about the role they may play in encouraging or suppressing different forms of organizational compliance efforts. Using theories of legal professionalism, I develop and test competing hypotheses regarding the moderating influence of lawyers on organizational compliance. I further seek to identify whether a key intra-professional difference – level of lawyer specialization – affects the strength of this moderation relationship. To test my hypotheses, I analyze immigrant employment authorization data before and after the issuance of a 2017 U.S. Citizenship and Immigration Services memo that revised the standards for evaluating certain H-1B visa applicants. Specifically, the memo suggested that applicants with the title “computer programmer” may not qualify for the visa unless the applicant’s proposed wage level clearly indicates the complexity of the job duties. Regression analyses show that visa applications filed with the assistance of lawyers were more likely to demonstrate a literal compliance strategy in the year following the memo (listing a wage level above the local median for computer programmers), while applications independently were more likely to display an creative compliance strategy (using an alternative job title). Applications filed with more-specialized lawyers are more likely to demonstrate a creative compliance response than those filed with less-specialized lawyers.