Self-rated health (SRH) is consistently related to mortality and morbidity. Yet, health ratings are subjective and reflect an individual's social context. Prior work has found differences in the structure of SRH—that is, in how self-assessments relate to underlying health conditions—across social groups, including by gender. However, prior work has not included transgender adults despite evidence that widespread interpersonal and structural stigma uniquely shapes their subjective experience of health. This study draws on information about 12 health conditions for a sample of transgender men, transgender women, nonbinary adults, cisgender men, and cisgender women. It examines whether the probabilities of reporting poor or fair SRH are similar among those with various underlying health problems. Findings reveal differences by gender identity and age group. For more than half of the examined conditions, self-rated health is poorer among nonbinary adults and younger transgender men than among other gender groups. These differences likely reflect distinct self-assessment processes that consider minority stress and structural stigma, as well as underlying differences in severity and comorbidity that stem from such stigma processes. SRH remains a useful, holistic measure of well-being, including for transgender groups.