Background: Supporting high school students’ career exploration, a critical aspect of college and career readiness, is a central concern for secondary school counselors. However, multilingual learners of English (MLs) face persistent barriers to participate in college and career readiness opportunities. Furthermore, research has reported that school counselors may require additional support and training on career exploration and working with MLs. Objectives: The purpose of this article is to examine how school counselors at a large urban high school provide career exploration experiences for MLs. Research Question: What systems, structures, and language-neutral policies supported or failed to support school counselors in providing career exploration for MLs in a large urban high school? Method: Drawing on critical ethnographic methods, I engaged in 10 months of fieldwork, which included recording fieldnotes, conducting interviews, and collecting documents and artifacts. Results and Conclusion: Drawing on theories of equity leadership, bureaucratic dysfunction, and language-neutral policy, I argue that three converging issues confounded school counselors’ efforts to provide career exploration opportunities for MLs: overwhelming caseloads, a lack of institutional knowledge about career exploration, and limited general support for MLs. Together, these systemic failures created a situation in which school counselors were unable to provide meaningful career exploration for MLs, despite their efforts. The article concludes with implications for school counselors around advocacy and addressing systemic issues that would better support their work with MLs.