Outlook 2013 prompts for password on new installs connecting to Exchange 2010

Hello all,

    I am running Exchange 2010 SP1 on my domain using a Windows 2008 R2 server on vmWare, and have clients using both Outlook 2010 and Outlook 2013. The clients running Outlook 2010 have no problems at all. They can download email, send email -- life is good. The same goes for clients who were upgraded to Outlook 2013 from Outlook 2010. My problem is occurring ONLY with clients who have a new install of Outlook 2013 -- clients who have never before had Outlook on their system.

    When these users try to receive or send mail in Outlook 2013, they receive a username/password prompt. I have checked that "Always prompt for logon credentials" is NOT checked. I have turned Cached Exchange Mode off, and unchecked "Connect to Exchange via HTTP" but neither of those made a difference. I have tried removing and re-creating the user's Outlook account and that helps for a few hours or days but then the problem returns.

    The only unusual thing about 2013 that I have never seen in 2010 is that when I add a new user account in Outlook, I receive a Security Alert about "The name on the security certificate is invalid or does not match the name of the site." I have tried answering Yes, No, and simply closing the alert without pressing a button, but it doesn't seem to make a difference. 

    I am using Basic authentication on my Exchange server. I have a Forefront TMG server as well and its authentication matches what Exchange uses.

    If there's any information I'm forgetting to provide please let me know and I'll be glad to help. My users are not at all happy with 2013 right now, and I'd like to show them that this problem can be defeated and that Outlook 2013 is really a good upgrade.

Thanks,

Nathanael

October 3rd, 2013 10:56am

Hi,

First, please check if you have checked Always promote for logon credentials option as shown in the picture below:

In addition, please try to remove the saved credential of Outlook to check the result .Please refer to the following steps:

1. Close Outlook

2. Click on Start > Control Panel

3. Click View by: and change it to Large icons

4. Click on Credential Manager

5. Under Windows Credentials and Generic Credentials you should see the entry of your email account.

6. Remove each of the entries from the Credential Manager vault and let Outlook prompt you for your updated password.

Regards.

Steve Fan
TechNet Community Support

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October 4th, 2013 3:12am

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