This study explored the role of gender identity and stigma among trans* individuals in their pursuit of healthcare support. Through in-depth, qualitative interviews with 17 trans* individuals, we observed intersections of individual, interpersonal, and institutional modes of stigma across a variety of contexts of trans* healthcare. In our findings, we examine three specific themes related to trans* individuals anxiety about seeking healthcare support—tough decisions, fear, and benevolent oppression—as well as potential directions for future improvement in trans* healthcare. Our findings reveal that trans* individuals apprehension about seeking healthcare support stems from a "big picture" account of trans* healthcare, wherein their own individual experiences are situated against the larger backdrop of anti-trans* discrimination, both inside and outside the context of healthcare. These findings illuminate the intersectional workings of stigma and their inhibiting role on trans* healthcare support seeking. Findings are interpreted in light of participant suggestions for more inclusive trans* healthcare practices and potential steps to address noted inequities in trans* healthcare support provision. [ABSTRACT FROM AUTHOR]