Researchers have concluded that policy implementation is a process of mutual adaptation between policies and implementers. Our study draws attention to that relationship, especially with respect to policies that challenge assumptions about sex, gender, and sexuality. We focus on how six administrators in one United States school district understood 'the work' of bringing the district's "Guidelines for Supporting Transgender and Gender Nonconforming Students" into practice. Our analysis of interview data focused these questions: How do administrators describe their motivation and commitment to engage in the work? What puzzles of practice do participants name? How do they talk about the work of implementation? What does that work mean/involve in everyday practice? What were their roles? We found that implementation was locally defined and enacted; participants' sense-making, their roles in enacting the Guidelines, and the puzzles they negotiated were influenced by their unique contexts. We share examples of diverse cases in an effort to create policy knowledge.