Exchange 2010 - Outlook keeps popping up asking for credentials

Environment:
Server side:

Windows SBS 2011
Exchange 2010
Client Side:
Outlook 2010
Windows XP / 7 Pro


Problem:
Outlook users continually have user credentials pop up appear

I have tried doing some research
Some of the solutions was to disable Outlook Anywhere in Outlook
un-ticking "connect to Microsoft Exchange using HTTP"
When you restart outlook, Outlook Anywhere is re-enabled

I am wondering what do i have to change server side to fix this issue,

Thanks in advance
Paul-Anthony DableyThinking Forward - Forward ThinkingAsked:
Who is Participating?
 
Simon Butler (Sembee)Connect With a Mentor ConsultantCommented:
As this is SBS 2011, you should have installed the certificate through SBS.
Easy to fix though - go through the SSL wizard in the SBS management console. Your trusted certificate should be available for you to select. Choose it and allow the wizard to complete.

Simon.
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R--RCommented:
First run outlook.exe /rpcdiag and check if outlook is connecting using http.
In outlook check the test-email autoconfiguration if there is any error.
Is the outlook is in the local network then uncheck "On Fast networks, Connect using HTTP first, then connect using TCP/IP”
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Paul-Anthony DableyThinking Forward - Forward ThinkingAuthor Commented:
Thanks R-R for your feedback
To me it looks like that it's connecting via TCPIP  (see attached)
The setting is already unchecked "On Fast networks, Connect using HTTP first, then connect using TCP/IP”

....
screenshot.fw.png
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dsnegi_25decCommented:
it looks totally a certificate issue.

Is issue with both windows ?
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Simon Butler (Sembee)ConsultantCommented:
The Outlook Anywhere setting is NOT the cause of this.
People go after that for some reason, find that it seems to work, when it hasn't really, because Autodiscover just puts the setting back. Just because the client is configured to use Outlook Anywhere doesn't mean it will.

The primary reason for this problem is, as already mentioned - SSL certificates.
Exchange 2010 (which is in SBS 2011) uses SSL certificates for all client communications, not just Outlook Anywhere. If there is a problem with the SSL certificate then Outlook will often throw an authentication prompt - mainly because it doesn't know what else to do.

Therefore the first question has to be - do you have a trusted SSL certificate on the server?
If so, was it installed through IIS, SBS or Exchange?

Simon.
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Md. MojahidCommented:
Check your ssl certificate and discuss with your ssl certificate provider.
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Paul-Anthony DableyThinking Forward - Forward ThinkingAuthor Commented:
Thanks everyone for your reply!
The SSL Certificate was purchased through DigiCert Unified Communications Certificate
and was installed through  Exchange
Would you suggest removing and reinstalling the certificate?
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