The pedagogical practice of connecting mathematical content to real world contexts, particularly contexts relevant to students' knowledge and experiences, can positively impact student motivation as well as promote conceptual understanding. However, little is known about how middle school teachers actually make relevant real world connections, and more specifically, the dilemmas and supports they encounter in this practice. Using a framework of dilemmatic spaces, this case study explored how one middle school teacher navigated the dilemmas that arose in her efforts to root her mathematics instruction in relevant real world contexts. Over 3 years, data collection efforts included beginning, middle, and end of year interviews, classroom observations with pre- and postlesson interviews, and the collection of student work and lesson-related artifacts. Using multiple and iterative data analysis techniques, we identified 3 larger dilemmas related to a lack of resources, finding alignment between student contributions and mathematical content, and leveraging real world contexts to support student learning.