As I understand it, Network Segments don't respect subnets and only look at a system's reported local IP to determine if it should run a specific policy or pull from a specific DP.
I've had problems if a user is at a location with an overlapping IP range. For example we use a 10.0.0.0/22 data LAN which overlaps with Apple's default for Airports. As Apple users, many of our employees have Airports at home and haven't changed their default IP scheme - why would they?
How can I get remote users to use an AWS cloud DP and local users to use the local JDS if Network Segments don't respect netmasks?
I have created a feature request of this topic: https://jamfnation.jamfsoftware.com/featureRequest.html?id=1392