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Occasionally, I have seen weird results sorting as well. When sorting into sub-groups, I try to give the parent group sorting criteria that matches any of the sub groups as well. As an example...
---Internal (10.0.0.0/8, 172.16.0.0/12, 192.168.0.0/16)
|--- Production (10.0.0.0/8)
|--- Development (172.16.0.0/12)
\--- Testing Lab (192.168.0.0/16)
--External (tag:DMZ, tag:VPN)
|--- DMZ (tag:DMZ)
\--- VPN (tag:VPN)
Also, you can control the Sorting Order between groups on the same level. So in the example above, when I select My Org., I can tell the External group to be evaluated first, then if the system doesn't match it'll continue to the Internal, and eventually fall through to the L&F if it doesn't match anything.
Thanks for the tips Joel. I was not yet fully aware of Sorting Order rearranging feature until your post. However I still do not feel sorting works well, because I have no other group that would qualify as landing place for DMZ clients. I wonder if this is one thing the Sorting Order can help with...
All our DMZ clients report correctly into ePO, and receive the DMZ tag. Yet when I test sort them, not all of them would go into a single group that has a sorting criteria no other group has.
I continue investigating...