Student well-being and behaviour is assessed daily by classroom teachers at school and teachers are also asked occasionally to complete evidence-based psychology reports regarding a particular student in their class to inform clinical practice and help with diagnoses. This critical qualitative study considers the role of surveillance in schools as a tool to keep students safe and ensure well-being. Data from a two-year qualitative study provides insight from teachers, administration and IT staff regarding the use of surveillance in schools and considers ways that data can be used to assist in cognitive behaviour therapy, as well as discussing the protection of data for vulnerable and marginalized students from a FOIPPA compliance perspective. Discussions emerge as to the potential use of data tracking and data collection for staff to identify and conduct cognitive behaviour therapy (CBT) in schools. The ability to use digital education records combined with advancements in technology might enable the same deep learning in education as in medicine in the areas self-regulation. Results from the study indicate. Information Technology (IT) staff struggle with their application of privacy matters and may not be using data tracking as a means to develop and document well-being for students and staff.