Monitoring applications (MAs) software provides filtering and monitoring for technology management. In the fall of 2020, a southeastern state encouraged public and charter K-12 schools to use MAs by providing funding for their purchase. This was intended to protect students from online threats and self-harm during the COVID-19 pandemic, which might increase due to the swell of online classes. This study examined the perceptions of high school students, teachers, technology facilitators, and technology directors on the MAs used in their schools and districts during and as a result of the COVID-19 pandemic. Inferential statistics modeling was used to analyze Likert scale answer results from 146 survey respondents. Open-ended answers were coded on semantic themes. Prominent differences amongst groups arose in perceptions towards MA prevention capabilities, and teachers exhibited differences in awareness of MA capabilities related to whether they received training. Implications for better MA design and implementation to fulfill intended purposes are discussed.