Transgender and gender diverse (TGD) people face a myriad of daily stressors because of the hegemonic gender norms embedded within U.S. society. Due to these minority stressors, TGD people report elevated anxiety, depression, stress, and suicidality, among other health issues. One mechanism through which stigma may lead to these negative mental health outcomes is through increased rumination. In this intensive daily diary study with 181 TGD individuals (ages 16–40), we gathered qualitative data on their ruminative thoughts over the course of 56 days. There were a total of 2,431 responses across participants, with individuals providing a range of 1–53 responses (M = 15 responses). Using an experiential framework and an inductive approach to thematic analysis, we generated the following themes: (a) interpersonal relationships as a site of struggle, (b) fear and worry in response to contextual factors, (c) the weight of basic needs and safety, (d) gender as experienced through self and others, (e) intersections of health and rumination, and (f) the occasional reprieve. Using a deductive approach, we also placed these data within the context of Bronfenbrenner’s Person–Process–Context–Time model to provide a conceptual model for future research in this area. These ruminative experiences revealed significant adversities and challenges weighing on participants’ minds that spanned many areas of life. These findings also highlight the nuanced nature of rumination for TGD individuals and areas that may be overlooked in current assessments of this construct. (PsycInfo Database Record (c) 2022 APA, all rights reserved)