Undocumented students find themselves on continuously shifting ground, calibrating each decision they make in accordance with or as a strategic reaction to the existing political climate. Specifically, some undocumented students find themselves in an ongoing internal battle to fashion an identity that both counters the pervasive stereotypes of undocumented people through a process of hyperdocumentation ("Chang in Harv Educ Rev" 81(3):508-520, 2011), while simultaneously bearing the weight of fierce anti-immigrant sentiment. In this article, we ask the following questions: How do Latinx undocumented students navigate educational spaces? In what ways do their legal statuses impact the production of their identities? How do they exert agency within the parameters of their undocumented status? In answering these questions, we explore the ways in which some undocumented students "figure"--or take agency in shaping meaning of--their worlds, find identity in their education, and leverage community cultural wealth (Yosso in "Race Ethn Educ" 8(1):69-91, 2005) as a source of critical hope and resilience in their quest to achieve the ever-nebulous American Dream.