Outlook 2010 Credentials never accepted - Exchange 2013 -

We have issues with Windows XP clients being prompted for network credentials over and over. Never allowing Outlook to open and connect. We have about 200 XP machine left in the environment unfortunately. Since we set up a hybrid CAS server in hopes to eventually start migrating mailboxes to Office 365, this issue started happening. All Windows 7 and greater running Office 2010 or greater aren't affected.

I know the XP and Office 2010 requirements are Office 2010 SP2 and Windows XP SP3. I have verified that they have this patch level.

Troubleshooting Steps taken;
  *   Installed updates to Windows XP SP3
  *   Installed updates to Office 2010 SP2
  *   Setting up a new Outlook profile
  *   Editing the Authentication settings(NTLM, Basic) and Encryption settings in the current Outlook profile

All our servers are Exchange 2013 CU6 on Windows Server 2012.

I am wondering if we need to run the Set-OutlookProvider command on the Exchange servers... but only article I can find is to do it on Exchange 2007. Wondering if anyone has had a need to and run this on the 2013 Exchange servers?

Set-OutlookProvider -Identity EXPR -CertPrincipalName msstd:*.contoso.com
Reference: https://technet.microsoft.com/en-us/library/cc535023(v=exchg.80).aspx

Could it hurt to run this on Exchange 2013 servers?

Thanks in advance.
Christian HansUndecided... Asked:
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Simon Butler (Sembee)ConsultantCommented:
First - Exchange 2013 CU6 is no longer supported. If you are in Hybrid then you must be on CU8 or CU9.

XP has problems with Exchange 2013, personally I wouldn't have advised migrating to Exchange 2013 until you removed XP.
It cannot cope with negotiate for authentication settings, so you need to set it to either NTLM or Basic. It also has problems with some of the SSL/TLS settings if you have attempted to shut those off.

Do you have a wildcard SSL certificate? If so then you need to run the command that you have posted for XP clients to work correctly.

Christian HansUndecided... Author Commented:
Thanks Simon, we don't have a wildcard in the certificate. Thats the other reason why Im questioning this.

We are unable to go to Exchange CU7 or higher because it will break our Cisco Unified Messaging services unfortunately.

The theory behind me wanting to do this is I have heard that WinXP and Office 2010 may have issues reading into an SSL Certificate, and it only reading the Friendly Name and not the Subject Alternative Names in the certificate. Hence the thought of editing the OulookProvider EXPR setting.

We have been using Exchange 2013 since it was released and haven't has any problems until we started going thru the Hybrid Configuration Wizard,
Simon Butler (Sembee)ConsultantCommented:
If you don't have a wildcard certificate, then the above command isn't appropriate.
For maximum compatibility, the URL for Outlook Anywhere, both internally and externally should be set to the same as the common name on the SSL certificate. If the SSL certificate has been issued with the root domain (example.com) as the common name, rather than something like host.example.com, then I would be looking to get the certificate reissued.

You should check with Cisco over support, because if you are in hybrid you are unsupported.


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