While qualitative research provides many insights into how gendered interactions operate at the level of interpersonal interactions and institutions, gender regimes, or political economic structures that shape inequality operate at the population level. It is now possible to look at the gender differences between the health of subpopulations beyond simple markers of “male” and “female,” and to see how sex assignment at birth, identity at adulthood, and differences in embodied expression factor into the advantages and disadvantages mediated by the gender regime through social determinants of health. Using a general health surveys of adults in the United States, I begin by analyzing the general patterns in self-rated health in a population-level sample of cisgender men and women, transgender men and women, and gender nonconforming respondents 31 U.S. states and Guam collected between 2014 and 2016. This research is the focus of Essay I, which is a rather straightforward survey-weighted regression analysis of the original data, forthcoming in Demography in December 2018. In Essay II, I exploit a significant shortcoming in the same survey’s design, in which the phone-based survey interviewers impute respondents’ sex based on the sound of their voices without confirming it in any manner throughout the rest of the survey (Riley, Blosnich, Bear, and Reisner 2017). This shortcoming provides quasi-experimental conditions in which phone interviewers have recorded their own overall voice-based assumptions about the sex of transgender respondents without first knowing that respondents are transgender. Key differences are discernable between transgender men who are rated consistently with their gender identity, and those who are not, as well as among transgender women. Essay III builds on the findings of Essay II about embodied characteristics, and explores how gender presentation may influence rates of identifying as transgender, and finds that racial/ethnic differences factor into the likelihood of identifying as transgender, after controlling for gender presentation. This essay uses data from the 2016 Minnesota Student Survey, a general survey of 9th and 11th graders in Minnesota Public schools.