Bumping this once before opening a ticket.
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Well that should definitely not be the case - I recommend you open a support ticket and mention this thwack thread so we can take a look!
Were you able to find a resolution to this? I just noticed I am having a similar issue. I've created new groups that don't seem to work and moving my user account between the groups I've set up leaves my logging into the original group I was in.
EDIT: I just saw your other post where you mentioned that removing the group from Orion and then adding it back worked. This worked for me as well.
I've got a case open for it (#964813). It's been taking a while to get a response, and the initial response I got doesn't seem like it should solve it. I asked them to confirm they had tested this proposed solution, but I have yet to hear back.
Development says that they can reproduce this issue. They believe it is caused by the caching of the SID within machine context can cause the issue. They would like you to try disabling the caching to see if it resolves your issue. To do that run the query below,
INSERT INTO [dbo].[WebSettings] VALUES ('UseMachineContext','false')
after you run the query, restart IIS and try replicating this issue. Let me know if you are still having issues or the query resolves the problem.