Older gay men commonly conceal their sexual identity in healthcare settings due to past experiences and expectations of encountering stigma and discrimination in these contexts. Although insights on how older gay men construct their sexual identity in healthcare may help contextualize this phenomenon, this question remains under-explored. Accordingly, we present the findings of a secondary grounded theory analysis of individual interview data, which we originally collected to examine the healthcare experiences of 27 gay men ages 50 and over, to explore constructions of sexual identity among the group. Our findings broadly reveal that older gay men’s varying exposure to intersecting systems of oppression, together with their perceptions of different healthcare settings, may be critical in shaping their constructions of sexual identity in these contexts. Our research supports the need for healthcare policies and practices that address stigma and discrimination as salient barriers to sexual identity disclosure among older gay men.