@John Biggston
1)Are your intranet boundary and VPN boundary separately placed in different boundary groups? If not, the error you described above may also occur.
2)A client is connected via VPN reports both the local network as well as the VPN network in inventory, in some cases the local network of VPN client may have the same IP address as the intranet client. Starting from the 2006 version, you can choose to directly create the VPN boundary type to avoid this situation.
There are two articles that provide more detailed instructions:
https://www.reddit.com/r/SCCM/comments/gs6x8r/vpn_boundaries_local_home_networks/
https://learn.microsoft.com/en-us/mem/configmgr/core/servers/deploy/configure/boundaries#vpn
3) >there is no record of it ever having an IP in our VPN subnets.
IP address is collected by two different things in ConfigMgr: heartbeat discovery and hardware inventory. You may check whether heartbeat discovery and hardware inventory are enabled.
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