In a wide variety of studies over the past two decades, the media has consistently been identified as a significant social institution implicated in normalizing and disseminating anti-Muslim prejudice. Identifying and combating Islamophobic discourses has been a challenging proposition, however, due to difficulties in systematically identifying and evaluating “Islamophobia” within texts. Islamophobia is a complex and contested phenomenon that defies easy classification within the boundaries of terminology which would normally be employed to describe hostility or prejudice based on, for example, race or religion. This article outlines some of the challenges involved in defining and categorizing Islamophobic discourses through an exploration of the process of constructing, evaluating, and applying a unique content analysis instrument, the “Islamophobia Index,” to media texts, using data sets drawn from the Australian news media. We critically reflect upon the methodological limitations of systematic quantitative studies, the importance of qualitative and interpretive approaches that take into account researcher subjectivities, and ultimately reposition and repurpose this project as a mixed-method study. In conclusion, potential applications for the Index, including non-media textual analysis, are considered.