The present study aims to identify factors that predict whether teachers engage in teaching about digital technologies (media education), which is an under-researched topic compared to the research about teaching with digital technologies (technology integration). Thus, a popular model of technology integration—the “will, skill, tool, pedagogy” model—guided our research on media education. Based on a survey of 2247 Swiss upper secondary school teachers, we found that for most of the media education topics, only a minority of teachers indicated that they have addressed them in class. Multilevel binomial regression analyses revealed that teachers’ responsibility beliefs (will) were one of the most important predictors of discussing media education topics. Furthermore, teachers’ self-assessed technical skills (skill) positively predicted whether they taught media literacy, whereas skills in teaching with digital technologies perceived by teachers (pedagogy) only promoted the likelihood that teachers would address topics of critical evaluation of online information and ethical questions of automation. The quality of the schools’ infrastructure (tool) seemed to be of minor importance or to have even detrimental effects in the context of media education. Moreover, we observed differences between subjects in engagement in media education, with language, arts, and humanities teachers being particularly more likely to cover aspects of media literacy in class.