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The U.S. government has invested millions of dollars into K–12 critical language education through domestic programs such as the National Security Agency’s STARTALK and study abroad programs like the Department of State’s National Security Language Initiative for Youth. These programs aim not only to jumpstart critical world language education, but furthermore to provide learners the amount of exposure needed to reach advanced levels of proficiency before college (Carroll, 1967; Isbell et al., 2019; c.f. Munoz, 2014). Despite the massive quantities of time and funding poured into early critical world language education, little is known about students’ experiences moving between levels of education. This is particularly true for less commonly taught languages (LCTL), where pre-tertiary learning is crucial for attaining higher proficiency levels. The current qualitative case study addresses this gap by examining the experiences of students learning Arabic as a second language across multiple stages and institutions. It explores how four students of Arabic make sense of their transition from high school to college-level world language studies. Data was collected via surveys and follow-up focus group interviews. As the current study was exploratory in nature, data analysis was approached openly rather than by starting with a pre-selected conceptual paradigm or theoretical account. Following an iterative process of open and axial coding, three major themes emerged. These themes collectively reveal that the educational juncture between high school language study to college classrooms can be a rocky experience for LCTL students. The first theme, Initial (Dis)Orientation, outlines how the focal students arrived on campus unaware of what their language study options were or how to even access them. This lack of awareness disempowered students from pursuing classes that matched their level and interest. The second theme, Classroom (Dis)Harmony, illustrates the ways in which students’ language learning backgrounds were often dismissed in their new pedagogical settings. Despite multiple years of high school study, students were regularly placed into classes inappropriate for their language skills. Finally, the last theme of Retrospective Appreciation discusses how students came to value their high school experiences in light of their university language programs. The contrast between grade-driven instruction at the college level and communicative/cultural instruction at the pre-tertiary level was demotivating for all four participants. The study concludes that the disjunctures experienced by the focal participants may undermine national efforts to build strong pipelines of language learners who can achieve higher levels of proficiency. Of the four focal participants, only one continued with Arabic study through the end of college. Finally, implications for educators are discussed. First, university programs seem to lack appropriate measures to evaluate and accommodate incoming pipeline learners. Likewise, high school programs are not doing enough to familiarize students with the learning opportunities ahead. The findings have implications for program administrators, teachers, and students on both sides of these periods of transition.