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Limited research considers the diversity within and across the binary dichotomy of gender identity. Using data from a large-scale survey of college-bound seniors, this study explores patterns in high school experiences, college aspirations, and perceived concerns among gender minority students. Results indicate there is a statistically significant difference between high school experiences based on gender identity, as gender minority students report less positive experiences. Concerns about college can also be divided into three constructs, including concerns about discrimination. While gender minority students worry more about discrimination overall, transgender students are more likely to report these concerns. Results emphasize the importance of identifying how student experiences may differ in order to strengthen support systems for those navigating the transition to college.