Over the past six years, the Pullias Center for Higher Education has been engaged in research designed to better understand the potential of digital tools to increase access to college. Their most recent $3.2 million "First in the World" (FITW) federal grant has enabled the Center to implement and evaluate an online game-based intervention in schools across the state of California. Beyond examining the effects of the game tool on college outcomes, the Center also collected and analyzed robust mixed methods data pertaining to college-going culture and digital infrastructure in California high schools serving low-income youth. The purpose of this document is to give a brief background on the Pullias Center's FITW study, introduce the data challenges we encountered during the study, and present four possible causes of these challenges based on interview and survey data.