Demographic and policy shifts in U.S. schools have contributed to English learners enrolling in schools with historically few English learners. This phenomenological study used interview data to identify dilemmas that one elementary teacher navigated while working with the sole English learner in her classroom. This context has the potential to inform the design of professional development for teachers working with English learners. Using a dilemmatic spaces framework, three dilemmas were identified related to whether to privilege professional experience or professional development, collaboration with the English as a Second Language (ESL) teacher, and how to navigate conflicting administrative expectations.