In our respective roles (one as a researcher, the other a program administrator), we have had dozens of conversations with English learners (ELs) preparing to graduate high school. In these conversations, we often encounter contradictory statements about EL teachers. As newcomers, students usually describe their EL teachers as "nice" and "helpful." Most say they would not have transitioned successfully into U.S. schools without EL teachers' support. However, many of these same students express concerns later on that EL teachers are holding them back from achieving their long-term educational goals (e.g., Shapiro, 2014Shapiro, , 2016. Students resent being placed in "sheltered" classes that feel socially isolating and academically unrigorous. They tell us, A growing body of educational research in TESOL has looked at the many roles that English language teachers serve within their institutions, including the prominent role of nurturer/caretaker (e.g., de Guerrero & Villamil, 2000;Farrell, 2011;Fritzen, 2011). Yet very little research has considered how the role of the EL teacher changes-or should change-over a student's educational trajectory. In this essay, we draw on conversations with secondary students and teachers to highlight the importance of a multifaceted, dynamic conception of EL teacher roles, particularly regarding their advocacy work with and for students. We emphasize three themes that are central to this conception of advocacy: aspiration, collaboration, and transparency. We conclude by discussing how this conception of advocacy as ethical care (Hos, 2014) plays out during intake, advising, curriculum development, and other pedagogical decision making.