Originally posted by Unknown
Set the group requirement that is not refreshing correctly, so that it is set to 'Can Expire' with the 'Expire Duration' to 1 days.
Update the 'Calculate Group Requirements' so that the 'Bypass Data View Cache' is set to Yes. 
Go back to the group, and you should be able to click 'Refresh Requirements' and see the updated requirements for the group member you are wanting to add.