On the system entitlement page, when attempting to upgrade the entitlements for my system, I selected "workgroup" from the list for each of the servers, then clicked the button to upgrade the entitlement info. two issues: 1. Since I couldnt of possibly upgraded anything to "workgroup", it shouldnt of been shown as an option. 2. when I did attempt to upgrade, I wasnt shown any error messages or warnings indicating that what I just did failed completely.
We've decided that adrian is looking at a magical org that had manually set options. Not replicable in proper orgs.
I have seen this as well, but with a hacked up Org. I'm not able to find this behavior on a real Org either. Will keep an eye out for it though.