In this reflective essay, Alberto Ledesma explores how being undocumented can produce a particular form of writer's block. He argues that there is a pattern of predictable silences and obfuscations inherent in all undocumented immigrant autobiographies that cannot be easily negotiated when undocumented students are asked to write about "their experiences." Ledesma contends that these patterns of silences often manifest as apparent rhetorical or mechanical errors in academic prose rather than intentional obfuscations meant to protect the writer's undocumented identity from being discovered. Reflecting on his own life experiences as a former undocumented student, Ledesma highlights that, paradoxically, the lifelong conditioning in silence may also interfere when undocumented writers are ready to render their authentic stories in public.