GoGuardian is a student monitoring tool that watches over twenty-seven million students across ten thousand schools, but what it does exactly, and how well it works, isn’t easy for students to know. To learn more about its functionality, accuracy, and impact on students, we filed dozens of public records requests and analyzed tens of thousands of results from the software. Using data from multiple schools in both red and blue states, what we uncovered was that, by design, GoGuardian is a red flag machine—its false positives heavily outweigh its ability to accurately determine whether the content of a site is harmful.