Hello Everyone,
We are approximately six months into Distance Education at our K12 institution and are looking to push out a payload to route all student iPad traffic through Cisco Umbrella. We are currently using Umbrella district wide both for on-campus network filtering and also for all Chromebook traffic (including at home).
We have successfully linked Umbrella with JAMF, as you can see in the below screenshot.

The downside we are seeing is that in order for the DNS routing to work you must install the Cisco Security Connector. This is fine and all, but it also appears that this application must be opened prior to any data following through OpenDNS? Has anybody run into a similar scenario and found a solution?
It feels like our department can do everything on our end to get this ready to go but if the student doesn't open this app at least once they will be able to browse unfiltered internet.
Here is the link to the official documentation from Cisco on deployment.

