I am using Cisco Umbrella/OpenDNS to filter for spam. VPNs were the problem for me and the solution was just to do a wildcard search with email notifications when they become a member of the policy. There is no restriction that I know of that can disable that little "i" button next to the network. In regards to WiFi whitelisting, I gave your scenario a test with the WiFi Whitelisting and my WiFi profile (both configured and scoped separately to the same device) got pushed before the whitelisting. Obviously, there are factors that play into this like network speed, servers, etc. But are you configuring that restriction within your WiFi Profile to make sure they are being pushed together?
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