Organizational/activational theory posits that transgender individuals should perform in the direction of their gender, not their sex, on cognitive tasks that show sex differences—the largest of which are observed on visuospatial tasks. Yet, tests of this hypothesis have been mixed for transgender men (TM). One possible reason is that performance shifts associated with the hormonal milieu at testing have not been fully considered in TM. Although “activating” influences, like gender-affirming hormone therapy (GAHT), are well-characterized in this population, endogenous ones, like ovarian cycling, have gone unaddressed. To provide a more complete picture of hormonal activation, we explored an influence of ovarian milieu on visuospatial performance of TM, and its potential contributions toward effects of sex and GAHT. We administered two male-favoring mental rotation tests (MRTs), and a sex-neutral control task to 22 TM naïve to GAHT (TM-), 29 TM receiving GAHT (TM+), and cisgender men (CM; n = 24) and women (CW; n = 43), testing cycling men (TM-) and women (CW) in either early follicular phase (Follicular) or midluteal phase (Luteal). On MRTs, performance of TM- varied across the menstrual cycle, and matched that of menstrual phase-matched CW. Additionally, cycling individuals in Follicular performed as strongly as TM+ and CM, all of whom performed above individuals in Luteal. Effects did not extend to a verbal control task, on which TM+ performed below others. Rather than conforming to static categories that suggest sex- or gender-typical organization of cognitive circuits, our findings support dynamic shifts in visuospatial ability of TM, and illustrate the need to consider activating effects of hormones beyond GAHT. •We explored an impact of ovarian milieu on mental rotation of transgender men (TM)•Performance of cycling TM mirrored menstrual phase-matched cisgender women•Follicular, not luteal, performance matched androgen-treated TM and cisgender men•On an estradiol-sensitive control task, androgen-treated TM performed below others•Visuospatial ability of TM may not be sex- or gender-typical—but hormone-responsive