This exploratory study used case study methods to identify whether value alignments between users and system features could be detected in an online digital badge system and learning environment, and if so, whether those value alignments could be said to affect use of the system. Values are “guiding principles of what people consider important in life” (Cheng & Fleischmann, 2010, n.p.) and are believed to have explanatory power in predicting behaviors and attitudes (Schwartz, 2007). A value sensitive design research method had to be devised anew to address the research questions and is arguably the major contribution of this study. First, a self-report scale (Portrait Values Questionnaire-RR) developed by Schwartz et al. (2012) was used to categorize the pragmatic values of teachers and administrators using the online VIF Learning Center badging into four higher order values: self-transcendence, conservation, openness to change, and self-enhancement. Statistically significant differences were found between male and female teachers, but not between teachers and administrators, nor between teachers mandated to use the system and those for whom use was optional. Second, the 19 values of Schwartz’s revised and refined theory of basic human values were used to assign human values to 11 feature-action pairs identified in the VIF Learning Center’s digital platform. Usage of the feature-action pairs was sparse, and data were spread unevenly, suggesting possible data loss or an indication that technical affordances were weak drivers of participation and engagement.