Monitoring applications (MAs) use digital and online tools to collect and track data on student behavior, and they have become increasingly popular among schools. Empirical research on these complex surveillance platforms is scant, and little is known about the efficacy or impact that they have on students. This study used a multi-method investigation: First, it conducted a thematic analysis of the purveyances of popular MAs, examining their datafication of students through three interrelated processes: Reduction, abstraction, and individualization. Second, it surveyed students who were in high school during the Pandemic about their experience with MAs during that time, using descriptive and inferential statistics to better understand the student perspective. This study offers several approaches for increasing awareness of MAs and their potential to datafy, as well as recommendations for further research on the efficacy and impact of MAs.