Trans-informed administrative guidance introduces concepts from trans studies to educational leaders, but researchers have relatively ignored these policy implementation tools. This content analysis describes the design of administrative guidance using a representative sample of 112 Illinois districts: the who, what, how, and why of supporting transgender students. The results substantiated evidence of trans-informed guidance that introduced complex gender "definitions" and legitimized students' identity. Many of these same texts also included barriers to supporting students with administrative gatekeeping, definitions reinforcing the gender binary, and mandates to involve parents in access decisions. All but one district (96%) highlighted existing state and local policies to motivate administrative actions around 13 issues. A minority of the texts provided specific directions to guide decision-making and reform efforts. This paper includes areas of concern and suggestions as policymakers initiate gender reforms.