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Password keeps prompt on clients for Outlook Anywhere 2013 published in TMG 2010?

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Hello Everyone,

This is information about my scenario:

I have Exchange Server 2013 installed on Windows Server 2012.

I have 2 x Mailbox Servers configured with one DAG, the 2 members are member of this DAG and only one DB has a copy on the second server.

I have 2 CAS Servers configured with NLB on Windows Server 2012.

The Exchange 2013 is configured with Outlook Anywhere with Basic authentication on the 2 load balanced CAS servers.

The internal outlook clients connect to Exchange Server 2013 using HTTPS without any issue.

OWA for Exchange 2013 is published on TMG 2010 and OWA is working fine for internal and external computers.

The used certificate is issued from AD CS, it is imported to all the 4 Exchange Server and to  TMG and it has all the required SANs.

The Root CA certificate and CRL files are imported to user/computer store for external computers.

The Outlook anywhere is published as well  on TMG 2010 and use the same web listener configured with OWA Publishing rule.

For OWA Publishing Rule I use FBA authentication in the listener and Basic authentication in the Authentication Delegation

For Outlook Anywhere Publishing rule I use FBA authentication in the listener (cuz it uses the same OWA publishing rule's listener) and Basic authentication for authentication delegation.

Now my issue is: On external machine not joined to domain with Windows 8 and Outlook 2013 I am trying to connect using Outlook Anywhere but it keeps asking me to type the username and password.

I have checked many things but still can't log-in, so can you help me in solving this issue?!!

Regards,



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