After an incident of inappropriate email contact between a teacher and student last school year, we looked into what more we could do as far as filtering and/or closely monitoring email for our students. Eventually we settled on using a service from Gaggle, but the road to get there was complex and with many lessons learned that we'd like to share. The presentation would cover the following topics: * Our initial response to the incident, messaging, and the ways what we were already doing worked (email archiver and good school counselors) * The first things we experimented with, and the hilarity that ensued with false positives and message volume * Why we went with Gaggle and a brief overview of their service and it's pros/cons * The limits of these technical solutions and the critical messaging we did with parents