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Error when you use the Remote Connectivity Analyzer tool to test Outlook Anywhere in an Office 365 environment: "Mutual Authentication could not be established"

Note The following scenario only applies to Microsoft Office 365 customers who have a hybrid deployment of on-premises Exchange Server and Exchange Online.

When you use the Microsoft Remote Connectivity Analyzer tool to test the Outlook Anywhere feature in a Microsoft Office 365 environment, the tool displays the following error message:
Mutual Authentication could not be established.
Additionally, a user may experience the following symptoms:
  • The user is repeatedly prompted for credentials and can't connect to Exchange Online by using Outlook Anywhere.
  • The user receives the following error message when he or she uses Microsoft Outlook 2010 or Microsoft Office Outlook 2007 to create the Outlook profile automatically:

    An encrypted connection to your mail server is not available. Click Next to attempt using an unencrypted connection.
This issue occurs if one or more of the following conditions are true:
  • The common name does not match the mutual authentication (msstd:) string that's entered in the Remote Connectivity Analyzer tool.
  • The mutual authentication string is valid. However, the CertPrincipalName attribute for the EXPR OutlookProvider object that's stored in Active Directory is invalid.

    Note The mutual authentication string equates to the Only connect to proxy servers that have this principal name in their certificate setting in the Exchange proxy settings in Outlook.
To resolve this issue, follow these steps:
  1. View the web server certificate that's installed on the Exchange 2010 hybrid deployment server, and confirm the common name to which the certificate was issued (for example,
  2. Open the Exchange proxy settings in Outlook, and check that the full qualified domain namd (FQDN) in the Mutual Authentication Principal Name field is entered correctly (for example, msstd:
  3. If it's necessary, run the following cmdlet by using Exchange Management Shell to change the CertPrincipalName attribute:
    Set-OutlookProvider EXPR -CertPrincipalName:""
The Remote Connectivity Analyzer tool negotiates a Secure Sockets Layer (SSL) connection to the remote host to retrieve various properties on X509 certificates. The tool evaluates the Subject attribute to identify the FQDN or common name that was assigned to the certificate (for example, 

For more information about the principal names, go to the following Microsoft Developer Network (MSDN) website: For more information about Exchange 2010 and Exchange 2007 Outlook providers, go to the following Microsoft websites:
Still need help? Go to the Office 365 Community website.

Article ID: 2710606 - Last Review: 11/21/2014 17:52:00 - Revision: 8.0

  • Microsoft Exchange Online
  • o365 o365e o365p o365a o365m hybrid KB2710606