Will I be told if a student's device is bypassing the web filter?
Yes. Skie reports a bypass of the filter, and a device that is not filtered appears in the dashboard against that exact device, with the breach centre carrying the alert. The device also reads each protection back from Android after every apply, so a missing filter lowers its compliance score.
Preventing a bypass is the first job. The filtering DNS is locked, Private DNS cannot be edited, VPN and proxy apps are never allowed, and other browsers are blocked. Detection is the second job, because an admin should hear about anything that gets through rather than assume.
Skie's reporting works at two levels. After each apply, the device reads the relevant protections back from Android and reports a compliance score. If the filter is not as it should be, the score drops and the device is visible. Separately, the breach centre collects events across every level, so a school admin, a branch head and the organisation admin each see what is in their scope.
Alerts are tied to the specific device, so you can tell which tablet and which student, rather than hunt through a list. You can sync and resolve at device, group, branch, school and organisation level. A missing check-in is a breach as well, which covers a device that went quiet.
One distinction matters. A network that blocks the encrypted DNS port is not a bypass. The dashboard flags it as a network condition, not a student action.
Email alerts and parent notification of alerts are not available yet, so the breach centre in the dashboard is where your staff check. Practical tip: put a short daily look at the breach centre into someone's routine, ideally the person who also owns the pilot.