This article examines the administrative and bureaucratic barriers faced by trans and nonbinary high-school students in the School District of Philadelphia. Despite strong gender-inclusive policies like the district's Policy 252, student interviews, first-hand observation, and document analysis reveal a variety of stress points that trans and nonbinary students still regularly face. This paper explores those "sticking points" individually and in detail through student experiences, from name and pronoun changes to bathrooms and written records, encouraging greater awareness among classroom teachers and school staff. Ultimately, the persistence of student challenges even amidst supportive policy -- itself far from a guarantee in many school districts -- suggests that gender inclusivity is not subject to single solutions, but rather requires care-filled consideration of stress points in our own distinct and ever-evolving contexts.