Exchange 2010 OOO not working but updates client and OWA

1.The issue is people who have OOO turned on can turn it off from either the Outlook client or OWA but it continues to send replies.
2. People can turn OOO on in Outlook client and it shows up in OWA that it was turned on with the correct settings, message, etc but nobody (in or out of the organization) receives an autoreply. This is affecting users across multiple databases (all on the same database server).
3. Setting up a OOO in OWA does not send out replies but it does show up in the outlook client that OOO is turned on.

So far it seems that several users that had trouble turning off replies were able to successfully clear the rules cache in Outlook and the AutoReplies stopped.

Exchange 2010 Standard on a CAS with UM role installed, Exchange 2010 Enterprise mailbox role.
https://testconnectivity.microsoft.com
Shows that...