Outlook Anywhere Trouble for new users

Hello,
My client had Exchange 2010 SP3, lastest rollup. He has Outlook Anywhere enabled and all of his users, except a new one he created a few days ago, have no problem accessing their mailboxes.
This new user experiences a problem, once she goes home and tries to open her Outlook 2010, a User\Password prompt appears which does not go away even when you get it right. Eventually after 3 attempts usually, it goes away but outlook opens up disconnected.
There is this Error event - MSExchangeAL id 8364, on the exchange server, and it does correspond to our problem. although, no valid solution is given for it, wherever i've searched.
We've tried Changing authentication methods from Basic to NTLM to Negotiate and to Basic back again, tried disabling the "Encrypt data between Outlook and Exchange", We've tries online mode, it does not even open outlook. it gives us an error regarding
a bad ost file. If outlook does allow the user in, it's only in cached mode and it immeditaly changes status from "Trying to connect..." to "Disconnected". We've checked the checkbox of "On slow connections use....". OWA Works.
Any insight would be greatly appreciated. Thank you.

Hi,
According to your description, only one your user cannot use Outlook Anywhere to connect to the server. If I misunderstand your meaning, please feel free to let me know.
If yes, I recommend you firstly troubleshoot if the issue is related to the certain Outlook client:
Recreate a new profile for the problematic users or change another computer to reconfigure the account.
Additionally, you can also use ExRCA to check the Outlook Anywhere connectivity:
https://testconnectivity.microsoft.com/
If you have any question, please feel free to let me know.
Thanks,
Angela Shi
TechNet Community Support

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