Exchange 2010 Outlook Anywhere continually prompts users for credentials

Posted on 2013-01-23
Last Modified: 2013-01-25
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.
Question by:argroup
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 3
  • 2
LVL 63

Accepted Solution

Simon Butler (Sembee) earned 500 total points
ID: 38812153
Wildcard certificates can be troublesome with Outlook Anywhere.

I presume you mean you have run this command:

Set-OutlookProvider expr -CertPrincipalName:"msstd:*"

Create a test account and run it through the Microsoft test site at 

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


Author Comment

ID: 38814324
There is already an autodiscover record setup for the existing server.
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 38814581
Have you run through the test site that I pointed to?


Author Comment

ID: 38814704
I did and it shows an error of:

Testing SSL mutual authentication with the RPC proxy server.
Verification of mutual authentication failed.
LVL 63

Expert Comment

by:Simon Butler (Sembee)
ID: 38819422
That would cause the problems you are seeing.
Are you using a wildcard SSL certificate by any chance?


Featured Post

Edgartown IT Case Study

Learn about Edgartown's quest to ensure the safety and security of the entire town's employee and citizen data. Read the case study!

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

This article aims to explain the working of CircularLogArchiver. This tool was designed to solve the buildup of log file in cases where systems do not support circular logging or where circular logging is not enabled
Check out this step-by-step guide for using the newly updated Experts Exchange mobile app—released on May 30.
To show how to generate a certificate request in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.:  First we need to log into the Exchange Admin Center. Navigate to the Servers >> Certificates…
Exchange organizations may use the Journaling Agent of the Transport Service to archive messages going through Exchange. However, if the Transport Service is integrated with some email content management application (such as an antispam), the admini…

691 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question