Increased use of technology in schools raises new privacy and security challenges for K-12 students—and harms such as commercialization of student data, exposure of student data in security breaches, and expanded tracking of students—but the extent of these challenges is unclear. In this paper, first, we interviewed 18 school officials and IT personnel to understand what educational technologies districts use and how they manage student privacy and security around these technologies. Second, to determine if these educational technologies are frequently endorsed across United States (US) public schools, we compiled a list of linked educational technology websites scraped from 15,573 K-12 public school/district domains and analyzed them for privacy risks. Our findings suggest that administrators lack resources to properly assess privacy and security issues around educational technologies even though they do pose potential privacy issues. Based on these findings, we make recommendations for policymakers, educators, and the CHI research community.