Outlook 2010 Mail Tips Could Not Be Retrieved / Out Of Office Doesn't work too.

Hi,
We have a small set up with 5 pc's and 1 server. All of the workstations are exactly the same.. specs,OS,software etc... 
One of the users is currently experiencing "Mail Tips Could Not Be Retrieved" issue. 
It shows up right above the SEND button when replying or sending a new e-mail.
Also Out Of Office / Automatic Replies function does not want to work as well. It asks me to try again later cause the server is not responding. 
The funny thing is that this is happening only to a single user.
Here is what I've tried:
- Tested E-Mail AutoConfiguration - Autodiscovery works fine and points to the right directory. 
- Deleted the profile and recreated it ... didn't work
-  Added the same mailbox to another computer - IT WORKED
- Checked all the SSL settings for each virtual folder in IIS and they are all set to IGNORE the certificate.
The other strange thing is that when I try to download the OAB from the affected PC a credential window pops up and asks for the username/password
of the particular mailbox.. Once I enter them the "Mail Tips could not be retrieved" message disappears and Out Of Office is accessible and ready to be used. 
Maybe Outlook 2010 setting or registry value ?

This sounds like an authentication issue for the Autodiscover/EWS URLs and your last paragraph basically confirmed it.
Is this PC domain joined and is this user logging on with his domain credentials and not locally to the computer?
Is the user able to access:
https://autodiscover.domain.com/autodiscover/autodiscover.xml
or
https://domain.com/autodicover/autodiscover.xml
An xml-page should be returned with ErrorCode 600 Invalid Request.
Is there a TMG or UAG server involved here?
Also check the proxy settings in Internet Options (if configured/required).
Robert Sparnaaij
[MVP-Outlook]
Outlook guides and more: HowTo-Outlook.com
Outlook Quick Tips: MSOutlook.info

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    4 ETW000                                                                                                  55  0.033039
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