Exchange 2010 Outlook Anywhere continually prompts users for credentials

I have an Exchange 2010 Server setup in an Exchange 2007 environment preparing for a complete migration. The certificate was purchased by someone other than myself. It is a wildcard certificate. OWA and ActiveSync work fine. However, Outlook Anywhere does not. I can setup the mailbox just fine and it finds the name of the mailbox. When in Outlook the user can send and receive email without issue but they are continually prompted for credentials. I've tried the set-outlook cmdlet to no avail. Any help would be greatly appreciated.
argroupAsked:
Who is Participating?
 
Simon Butler (Sembee)Connect With a Mentor ConsultantCommented:
Wildcard certificates can be troublesome with Outlook Anywhere.

I presume you mean you have run this command:

Set-OutlookProvider expr -CertPrincipalName:"msstd:*.example.net"

Create a test account and run it through the Microsoft test site at http://exrca.com/ 

The credential prompt could be autodiscover. Have you setup an autodiscover host name in your DNS to point to the server?

Simon.
0
 
argroupAuthor Commented:
There is already an autodiscover record setup for the existing server.
0
 
Simon Butler (Sembee)ConsultantCommented:
Have you run through the test site that I pointed to?

Simon.
0
 
argroupAuthor Commented:
I did and it shows an error of:


Testing SSL mutual authentication with the RPC proxy server.
Verification of mutual authentication failed.
0
 
Simon Butler (Sembee)ConsultantCommented:
That would cause the problems you are seeing.
Are you using a wildcard SSL certificate by any chance?

Simon.
0
Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.

All Courses

From novice to tech pro — start learning today.