Current research suggests that attention to language variation in teacher preparation can promote equity and narrow achievement gaps, particularly for African American students. However, persistent ideologies about language and race can stymie teachers’ desires for equitable teaching.Teachers who take up linguistically responsive positions that value student language variation still struggle in the moments of enactment due to expectations that they serve as gatekeepers for “standard” English(es). In this article, I conceptualize these struggles as linguistic ideological dilemmas (LIDs) and use discourse analytic and qualitative methods to present illustrations of preservice English teachers’ LIDs as they grapple with deficit language ideologies in relation to course work about language variation. In the focal illustration, I use positioning theory to illustrate the LIDs faced by a student teacher when responding to a student’s blog writing that included features of African American English. The findings show how this participant and others hadlimited awareness of how they were positioned racially until the moment of teaching in which they struggled to articulate and enact linguistically informed principles; in some cases, this positionality led to avoidance of future discussions of race and language. The findings advance past scholarship through generative description of students’ internalized deficit language ideologies and teachers’ struggles with implementation related to valuing language variation. Findings show the affordances and limitations of code-switching for addressing language variation in classroom interactions and the need for preparation about when, how, and why to have conversations about language variation, including greater understanding of language-related ideological triggers.